Total synthesis of (+)-nojirimycin and (+)-1-deoxynojirimycin

H Iida, N Yamazaki, C Kibayashi

Index: Iida, Hideo; Yamazaki, Naoki; Kibayashi, Chihiro Journal of Organic Chemistry, 1987 ,  vol. 52,  # 15  p. 3337 - 3342

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Citation Number: 135

Abstract

An efficient chiral total synthesis of (+)-nojirimycin (1) and (+)-1-deoxynojirimycin (2) has been achieved in optically pure form via the common intermediate 11 derived from the nonsugar chiral pool. The monosilyl derivative 4 of 2, 3-0-isopropylidene-~-threitol (3) was converted to the (E)-allyl alcohol 8, which upon asymmetric epoxidation provided the syn epoxide 9. Regio-and stereoselective epoxide opening reaction of 9 followed by ...

 Related Synthetic Route
Methanesulfonyl chloride Structure

124-63-0

Methanesulfonyl...

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexan-1-ol Structure

108818-04-8

(2S,3S,4R,5R)-5...

~97%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)-1-<(methylsulfonyl)oxy>hexane Structure

108818-05-9

(2S,3S,4R,5R)-5...

(E)-(4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-4,5-O-(1-methylethylidene)-2-hexen-1-ol Structure

108818-00-4

(E)-(4S,5S)-6-<...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)-1-<(methylsulfonyl)oxy>hexane Structure

108818-05-9

(2S,3S,4R,5R)-5...

(2S,3R,4R,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol Structure

108818-01-5

(2S,3R,4R,5S)-6...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)-1-<(methylsulfonyl)oxy>hexane Structure

108818-05-9

(2S,3S,4R,5R)-5...

[(4S,5S)-5-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Structure

108817-96-5

[(4S,5S)-5-({[(...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)-1-<(methylsulfonyl)oxy>hexane Structure

108818-05-9

(2S,3S,4R,5R)-5...

(E)-methyl 3-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate Structure

108817-99-8

(E)-methyl 3-((...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)-1-<(methylsulfonyl)oxy>hexane Structure

108818-05-9

(2S,3S,4R,5R)-5...

(2R,3R,4S,5S)-2-azido-6-<(tert-butyldimethylsilyl)oxy>-4,5-(isopropylidenedioxy)hexane-1,3-diol Structure

108818-02-6

(2R,3R,4S,5S)-2...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)-1-<(methylsulfonyl)oxy>hexane Structure

108818-05-9

(2S,3S,4R,5R)-5...

(2S,3S,4R,5R)-5-azido-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexane Structure

108818-03-7

(2S,3S,4R,5R)-5...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)-1-<(methylsulfonyl)oxy>hexane Structure

108818-05-9

(2S,3S,4R,5R)-5...

(2S,3S,4R,5R)-5-azido-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexane Structure

108818-03-7

(2S,3S,4R,5R)-5...

~97%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexan-1-ol Structure

108818-04-8

(2S,3S,4R,5R)-5...

(E)-(4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-4,5-O-(1-methylethylidene)-2-hexen-1-ol Structure

108818-00-4

(E)-(4S,5S)-6-<...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexan-1-ol Structure

108818-04-8

(2S,3S,4R,5R)-5...

(2S,3R,4R,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol Structure

108818-01-5

(2S,3R,4R,5S)-6...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexan-1-ol Structure

108818-04-8

(2S,3S,4R,5R)-5...

[(4S,5S)-5-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Structure

108817-96-5

[(4S,5S)-5-({[(...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexan-1-ol Structure

108818-04-8

(2S,3S,4R,5R)-5...

(E)-methyl 3-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate Structure

108817-99-8

(E)-methyl 3-((...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexan-1-ol Structure

108818-04-8

(2S,3S,4R,5R)-5...

(2R,3R,4S,5S)-2-azido-6-<(tert-butyldimethylsilyl)oxy>-4,5-(isopropylidenedioxy)hexane-1,3-diol Structure

108818-02-6

(2R,3R,4S,5S)-2...

~%

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexan-1-ol Structure

108818-04-8

(2S,3S,4R,5R)-5...

(E)-(4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-4,5-O-(1-methylethylidene)-2-hexen-1-ol Structure

108818-00-4

(E)-(4S,5S)-6-<...

~%

(2S,3S,4R,5R)-5-azido-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexane Structure

108818-03-7

(2S,3S,4R,5R)-5...

(2S,3R,4R,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol Structure

108818-01-5

(2S,3R,4R,5S)-6...

~%

(2S,3S,4R,5R)-5-azido-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexane Structure

108818-03-7

(2S,3S,4R,5R)-5...

[(4S,5S)-5-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Structure

108817-96-5

[(4S,5S)-5-({[(...

~%

(2S,3S,4R,5R)-5-azido-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexane Structure

108818-03-7

(2S,3S,4R,5R)-5...

(E)-methyl 3-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate Structure

108817-99-8

(E)-methyl 3-((...

~%

(2S,3S,4R,5R)-5-azido-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexane Structure

108818-03-7

(2S,3S,4R,5R)-5...

(2S,3R,4R,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol Structure

108818-01-5

(2S,3R,4R,5S)-6...

~49%

(2R,3R,4S,5S)-2-azido-6-<(tert-butyldimethylsilyl)oxy>-4,5-(isopropylidenedioxy)hexane-1,3-diol Structure

108818-02-6

(2R,3R,4S,5S)-2...

(E)-(4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-4,5-O-(1-methylethylidene)-2-hexen-1-ol Structure

108818-00-4

(E)-(4S,5S)-6-<...

~%

(2R,3R,4S,5S)-2-azido-6-<(tert-butyldimethylsilyl)oxy>-4,5-(isopropylidenedioxy)hexane-1,3-diol Structure

108818-02-6

(2R,3R,4S,5S)-2...

[(4S,5S)-5-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Structure

108817-96-5

[(4S,5S)-5-({[(...

~%

(2R,3R,4S,5S)-2-azido-6-<(tert-butyldimethylsilyl)oxy>-4,5-(isopropylidenedioxy)hexane-1,3-diol Structure

108818-02-6

(2R,3R,4S,5S)-2...

(E)-methyl 3-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate Structure

108817-99-8

(E)-methyl 3-((...

~%

(2R,3R,4S,5S)-2-azido-6-<(tert-butyldimethylsilyl)oxy>-4,5-(isopropylidenedioxy)hexane-1,3-diol Structure

108818-02-6

(2R,3R,4S,5S)-2...

[(4S,5S)-5-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Structure

108817-96-5

[(4S,5S)-5-({[(...

~%

(2S,3R,4R,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol Structure

108818-01-5

(2S,3R,4R,5S)-6...

(E)-methyl 3-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate Structure

108817-99-8

(E)-methyl 3-((...

~%

(2S,3R,4R,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol Structure

108818-01-5

(2S,3R,4R,5S)-6...

(E)-methyl 3-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate Structure

108817-99-8

(E)-methyl 3-((...

~83%

(E)-(4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-4,5-O-(1-methylethylidene)-2-hexen-1-ol Structure

108818-00-4

(E)-(4S,5S)-6-<...

[(4S,5S)-5-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Structure

108817-96-5

[(4S,5S)-5-({[(...

~%

(E)-methyl 3-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate Structure

108817-99-8

(E)-methyl 3-((...

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)-1-<(methylsulfonyl)oxy>hexane Structure

108818-05-9

(2S,3S,4R,5R)-5...

~94%

(2R,3R,4S,5S)-4,5-(isopropylenedioxy)-3-(methoxymethoxy)-2-<(methoxymethoxy)methyl>piperidine Structure

108818-06-0

(2R,3R,4S,5S)-4...

(E)-(4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-4,5-O-(1-methylethylidene)-2-hexen-1-ol Structure

108818-00-4

(E)-(4S,5S)-6-<...

~%

(2R,3R,4S,5S)-4,5-(isopropylenedioxy)-3-(methoxymethoxy)-2-<(methoxymethoxy)methyl>piperidine Structure

108818-06-0

(2R,3R,4S,5S)-4...

(2S,3R,4R,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol Structure

108818-01-5

(2S,3R,4R,5S)-6...

~%

(2R,3R,4S,5S)-4,5-(isopropylenedioxy)-3-(methoxymethoxy)-2-<(methoxymethoxy)methyl>piperidine Structure

108818-06-0

(2R,3R,4S,5S)-4...

[(4S,5S)-5-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Structure

108817-96-5

[(4S,5S)-5-({[(...

~%

(2R,3R,4S,5S)-4,5-(isopropylenedioxy)-3-(methoxymethoxy)-2-<(methoxymethoxy)methyl>piperidine Structure

108818-06-0

(2R,3R,4S,5S)-4...

(E)-methyl 3-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate Structure

108817-99-8

(E)-methyl 3-((...

~%

(2R,3R,4S,5S)-4,5-(isopropylenedioxy)-3-(methoxymethoxy)-2-<(methoxymethoxy)methyl>piperidine Structure

108818-06-0

(2R,3R,4S,5S)-4...

(2R,3R,4S,5S)-2-azido-6-<(tert-butyldimethylsilyl)oxy>-4,5-(isopropylidenedioxy)hexane-1,3-diol Structure

108818-02-6

(2R,3R,4S,5S)-2...

~%

(2R,3R,4S,5S)-4,5-(isopropylenedioxy)-3-(methoxymethoxy)-2-<(methoxymethoxy)methyl>piperidine Structure

108818-06-0

(2R,3R,4S,5S)-4...

(2S,3S,4R,5R)-5-azido-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexan-1-ol Structure

108818-04-8

(2S,3S,4R,5R)-5...

~%

(2R,3R,4S,5S)-4,5-(isopropylenedioxy)-3-(methoxymethoxy)-2-<(methoxymethoxy)methyl>piperidine Structure

108818-06-0

(2R,3R,4S,5S)-4...


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