General syntheses of 2', 3'-dideoxynucleosides and 2', 3'-didehydro-2', 3'-dideoxynucleosides

…, Y Kosugi, KC Pullaiah, P Van Roey

Index: Chu; Bhadti; Doboszewski; Gu; Kosugi; Pullaiah; Van Roey Journal of Organic Chemistry, 1989 ,  vol. 54,  # 9  p. 2217 - 2225

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Citation Number: 142

Abstract

A general synthetic method for 2', 3'-unsaturated nucleosides from the corresponding ribonucleosides is described. The 5'-0-silyl protected ribonucleosides were converted to the bisxanthates by reaction with carbon disulfide, followed by alkylation. The bisxanthates on reduction with tri-n-butyltin hydride and deprotection of the 5'-O-silyl group afforded the unsaturated nucleosides. The desulfurization of cyclic thionocarbonates has also been ...

 Related Synthetic Route
N4-acetyl-2',3'-didehydro-2',3'-dideoxycytidine Structure

119794-43-3

N4-acetyl-2',3'...

~70%

Dideoxycytidinene Structure

7481-88-1

Dideoxycytidinene

N4-acetyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine Structure

119794-42-2

N4-acetyl-5'-O-...

~%

Dideoxycytidinene Structure

7481-88-1

Dideoxycytidinene

5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-[[(β-cyanoethyl)thio]thiocarbonyl]-5-methyluridine Structure

119794-53-5

5'-O-(tert-buty...

~67%

1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine Structure

119794-55-7

1-(5-O-tert-but...

5'-O-(tert-butyldimethylsilyl)-5-methyl-2',3'-O-thionocarbonyluridine Structure

119794-54-6

5'-O-(tert-buty...

~53%

1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine Structure

119794-55-7

1-(5-O-tert-but...

5'-O-TBDMS-thymidine Structure

119794-52-4

5'-O-TBDMS-thymidine

~%

1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine Structure

119794-55-7

1-(5-O-tert-but...

5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine Structure

119794-39-7

5'-O-(tert-buty...

~86%

N2-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine Structure

119794-40-0

N2-isobutyryl-2...

5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-O-thionocarbonylguanosine Structure

119794-38-6

5'-O-(tert-buty...

~%

N2-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine Structure

119794-40-0

N2-isobutyryl-2...

5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-bis-O-[(methylthio)thiocarbonyl]guanosine Structure

119794-50-2

5'-O-(tert-buty...

~%

N2-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine Structure

119794-40-0

N2-isobutyryl-2...

5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-bis-O-[[(β-cyanoethyl)thio]thiocarbonyl]guanosine Structure

119794-37-5

5'-O-(tert-buty...

~%

N2-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine Structure

119794-40-0

N2-isobutyryl-2...

5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-bis-O-[[(β-cyanoethyl)thio]thiocarbonyl]guanosine Structure

119794-37-5

5'-O-(tert-buty...

~57%

5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine Structure

119794-39-7

5'-O-(tert-buty...

5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-bis-O-[(methylthio)thiocarbonyl]guanosine Structure

119794-50-2

5'-O-(tert-buty...

~53%

5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine Structure

119794-39-7

5'-O-(tert-buty...

5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-O-thionocarbonylguanosine Structure

119794-38-6

5'-O-(tert-buty...

~49%

5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine Structure

119794-39-7

5'-O-(tert-buty...

5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-[[(β-cyanoethyl)thio]thiocarbonyl]uridine Structure

119794-47-7

5'-O-(tert-buty...

~89%

1-((2R,5S)-5-((tert-butyldimethylsilyloxy)methyl)-2,5-dihydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119794-49-9

1-((2R,5S)-5-((...

5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-[[(β-cyanoethyl)thio]thiocarbonyl]inosine Structure

119794-35-3

5'-O-(tert-buty...

~87%

5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxyinosine Structure

119818-51-8

5'-O-(tert-buty...

D-2',3'-O-thiocarbonylene-5'-O-tert-butyldimethylsilyl inosine Structure

119794-36-4

D-2',3'-O-thioc...

~40%

5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxyinosine Structure

119818-51-8

5'-O-(tert-buty...

N4-acetyl-2',3'-didehydro-2',3'-dideoxycytidine Structure

119794-43-3

N4-acetyl-2',3'...

~80%

N4-acetyl-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine Structure

119818-52-9

N4-acetyl-1-(2,...

2'-TBDMS-Ac-rC Structure

119794-51-3

2'-TBDMS-Ac-rC

~%

N4-acetyl-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine Structure

119818-52-9

N4-acetyl-1-(2,...

N4-acetyl-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-[(methylthio)thiocarbonyl]cytidine Structure

119794-41-1

N4-acetyl-5'-O-...

~%

N4-acetyl-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine Structure

119818-52-9

N4-acetyl-1-(2,...

N4-acetyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine Structure

119794-42-2

N4-acetyl-5'-O-...

~86%

N4-acetyl-2',3'-didehydro-2',3'-dideoxycytidine Structure

119794-43-3

N4-acetyl-2',3'...

2'-TBDMS-Ac-rC Structure

119794-51-3

2'-TBDMS-Ac-rC

~%

N4-acetyl-2',3'-didehydro-2',3'-dideoxycytidine Structure

119794-43-3

N4-acetyl-2',3'...

N4-acetyl-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-[(methylthio)thiocarbonyl]cytidine Structure

119794-41-1

N4-acetyl-5'-O-...

~%

N4-acetyl-2',3'-didehydro-2',3'-dideoxycytidine Structure

119794-43-3

N4-acetyl-2',3'...

N4-acetyl-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-[(methylthio)thiocarbonyl]cytidine Structure

119794-41-1

N4-acetyl-5'-O-...

~62%

N4-acetyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine Structure

119794-42-2

N4-acetyl-5'-O-...


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