Chemistry Letters

Chemical synthesis of deoxysepiapterin.

R Baur, T Sugimoto, W Pfleiderer

Index: Baur, Ralph; Sugimoto, Takashi; Pfleiderer, Wolfgang Chemistry Letters, 1984 , p. 1025 - 1028

Full Text: HTML

Citation Number: 10

Abstract

A chemical synthesis of the yellow eye pigment deoxysepiapterin of Drosophila melanogaster has been achieved from 7-alkylthio pteridines by homolytic nucleophilic acylation at C-6 and subsequent hydrolyses to 6-propionylpterin derivatives followed by desulfurizations with copper–aluminum alloy.

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

92180-37-5

2-amino-4-(pent...

~%

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

71014-28-3

2-amino-6-propa...

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

92180-40-0

2-amino-7-(meth...

~0%

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)-...

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

71014-28-3

2-amino-6-propa...

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

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

26212-13-5

2,4-diaminopter...

~%

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

71014-28-3

2-amino-6-propa...

2,4-diaminopteridine-7-thiol Structure

92180-34-2

2,4-diaminopter...

~%

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

71014-28-3

2-amino-6-propa...

2,4-diamino-7-chloropteridine Structure

92180-32-0

2,4-diamino-7-c...

~%

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

71014-28-3

2-amino-6-propa...

2,4-diamino-7-(methylthio)pteridine Structure

92180-36-4

2,4-diamino-7-(...

~%

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

71014-28-3

2-amino-6-propa...

2,4-diamino-7-(methylthio)-6-propionylpteridine Structure

92180-38-6

2,4-diamino-7-(...

~%

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

71014-28-3

2-amino-6-propa...

2-Amino-4-(pentyloxy)pteridin-7(8H)-thion Structure

92180-33-1

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-propionyl-7-(propylthio)pteridine Structure

92180-37-5

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)-6-propionylpteridine Structure

92180-41-1

2-amino-4-(pent...

2-Amino-4-(pentyloxy)pteridin-7(8H)-thion Structure

92180-33-1

2-Amino-4-(pent...

~%

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

92180-42-2

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

Ethanol Structure

64-17-5

Ethanol

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

92180-37-5

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)-6-propionylpteridine Structure

92180-41-1

2-amino-4-(pent...

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

49560-67-0

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...

~28%

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)-...

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

71014-28-3

2-amino-6-propa...

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

Detail
2,4-diaminopteridine-7-thiol Structure

92180-34-2

2,4-diaminopter...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2,4-diamino-7-chloropteridine Structure

92180-32-0

2,4-diamino-7-c...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2,4-diamino-7-(methylthio)pteridine Structure

92180-36-4

2,4-diamino-7-(...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2,4-diamino-7-(methylthio)-6-propionylpteridine Structure

92180-38-6

2,4-diamino-7-(...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin

2-Amino-4-(pentyloxy)pteridin-7(8H)-thion Structure

92180-33-1

2-Amino-4-(pent...

~%

deoxysepiapterin Structure

1797-87-1

deoxysepiapterin


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