Helvetica chimica acta

Pteridines. Part LXXXV. Chemical synthesis of deoxysepiapterin and 6??acylpteridines by acyl radical substitution reactions

R Baur, T Sugimoto, W Pfleiderer

Index: Baur, Ralph; Sugimoto, Takashi; Pfleiderer, Wolfgang Helvetica Chimica Acta, 1988 , vol. 71, p. 531 - 543

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Citation Number: 21

Abstract

Abstract A new synthesis of deoxysepiapterin (2), one of the two yellow eye pigments of the Drosophila mutant sepia, is described. The synthetic approach makes use of a homolytic nucleophilic acylation of 7-(alkylthio) pteridine derivatives (11, 13, 15, 18, 20) leading to the corresponding 6-acyl derivatives (21–27). Desulfurizations have been achieved for the first time in the pteridine series using Raney-Co, Raney-Cu, or Cu [BOND] Al alloy in alkaline ...

 Related Synthetic Route
2-amino-4-(pentyloxy)-6-propionylpteridine Structure

92180-41-1

2-amino-4-(pent...

~85%

2-amino-6-propanoyl-1H-pteridin-4-one Structure

71014-28-3

2-amino-6-propa...

2-amino-4-(pentyloxy)-7-chloropteridine Structure

92180-31-9

2-amino-4-(pent...

~%

2-amino-6-propanoyl-1H-pteridin-4-one Structure

71014-28-3

2-amino-6-propa...

2-amino-4-(pentyloxy)-7-(propylthio)pteridine Structure

92180-35-3

2-amino-4-(pent...

~%

2-amino-6-propanoyl-1H-pteridin-4-one Structure

71014-28-3

2-amino-6-propa...

2-amino-4-(pentyloxy)pteridin-7(8H)-one Structure

49560-67-0

2-amino-4-(pent...

~%

2-amino-6-propanoyl-1H-pteridin-4-one Structure

71014-28-3

2-amino-6-propa...

2-amino-4-(pentyloxy)-6-propionylpteridine-7-thiol Structure

92180-39-7

2-amino-4-(pent...

~%

2-amino-6-propanoyl-1H-pteridin-4-one Structure

71014-28-3

2-amino-6-propa...

benzyl (1R,6R)-2-(1,2-dihydroxypropan-2-yl)-9-azabicyclo[4.2.1]non-2-ene-9-carboxylate Structure

69022-85-1

benzyl (1R,6R)-...

~80%

2-amino-6-propanoyl-1H-pteridin-4-one Structure

71014-28-3

2-amino-6-propa...

2-amino-4-(pentyloxy)-7-chloropteridine Structure

92180-31-9

2-amino-4-(pent...

~%

1-(2-amino-4-ethoxypteridin-6-yl)propan-1-one Structure

92180-42-2

1-(2-amino-4-et...

2-amino-4-(pentyloxy)-7-(propylthio)pteridine Structure

92180-35-3

2-amino-4-(pent...

~%

1-(2-amino-4-ethoxypteridin-6-yl)propan-1-one Structure

92180-42-2

1-(2-amino-4-et...

2-amino-4-(pentyloxy)pteridin-7(8H)-one Structure

49560-67-0

2-amino-4-(pent...

~%

1-(2-amino-4-ethoxypteridin-6-yl)propan-1-one Structure

92180-42-2

1-(2-amino-4-et...

2-amino-6-propanoyl-1H-pteridin-4-one Structure

71014-28-3

2-amino-6-propa...

~31%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2-amino-4-(pentyloxy)-7-chloropteridine Structure

92180-31-9

2-amino-4-(pent...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2-amino-4-(pentyloxy)-7-(propylthio)pteridine Structure

92180-35-3

2-amino-4-(pent...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2-amino-4-(pentyloxy)-6-propionyl-7-(propylthio)pteridine Structure

92180-37-5

2-amino-4-(pent...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2-amino-4-(pentyloxy)-6-propionylpteridine-7-thiol Structure

92180-39-7

2-amino-4-(pent...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2-amino-7-(methylthio)-6-propionylpteridin-4(3H)-one Structure

92180-40-0

2-amino-7-(meth...

~38%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2,4-diaminopteridin-7(8H)-one Structure

26212-13-5

2,4-diaminopter...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2-amino-4-(pentyloxy)-6-propionylpteridine Structure

92180-41-1

2-amino-4-(pent...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

benzyl (1R,6R)-2-(1,2-dihydroxypropan-2-yl)-9-azabicyclo[4.2.1]non-2-ene-9-carboxylate Structure

69022-85-1

benzyl (1R,6R)-...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin


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