294198-57-5

Basic information

• Product Name: (-)-dibenzyl macrosphelide A
• Synonyms: (-)-dibenzyl macrosphelide A
• CAS NO: 294198-57-5
• Molecular Weight: 522.595
• Mol File: 294198-57-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (-)-dibenzyl macrosphelide A(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-dibenzyl macrosphelide A(294198-57-5)
• EPA Substance Registry System: (-)-dibenzyl macrosphelide A(294198-57-5)

Safety Data

• Hazardous Substances Data: 294198-57-5(Hazardous Substances Data)

Upstream product

• 294198-54-2 (E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester 
• 294198-55-3 (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester 
• 294198-51-9 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester 
• 294198-52-0 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester 
• 295788-39-5 2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoate 
• 294198-50-8 2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 
• 434938-20-2 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-[(S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethoxycarbonyl]-but-3-enyl ester 
• 434938-21-3 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-[(S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethoxycarbonyl]-but-3-enyl ester 
• 434938-27-9 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-2-[(E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyloxycarbonyl]-1-methyl-ethyl ester 
• 434938-18-8 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester 
• 434938-19-9 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester 
• 459809-90-6 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (S)-2-((E)-(1S,2R)-2-benzyloxy-4-methoxycarbonyl-1-methyl-but-3-enyloxycarbonyl)-1-methyl-ethyl ester 
• 459809-78-0 (E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid methyl ester 
• 459809-71-3 (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester 

Downstream Products

• 172923-77-2 (+)-macrosphelide A 

Relevant articles and documents

Formal total synthesis of macrosphelide (+)-A, effect on macrolactonization depended upon the lactone formation position

Formal total synthesis of (+)-macrosphelide A (1) was achieved based on macrolactonization via path B from a seco-acid (3) and path C from a seco-acid (4). The yield of macrolactonization via paths B and C were 18 and 59%, respectively.

Total syntheses of macrosphelides (+)-A, (-)-A and (+)-E

Total syntheses of (+)-macrosphelide A 1 (18.5% overall yield in 11 steps) and (+)-macrosphelide E 2 (23.9% overall yield in 11 steps) have been achieved via the chemoenzymatic reaction product (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 4. The enantiomer (-)-A (1) (14.2% overall yield in 11 steps) of (+)-1 was also synthesized from the chemoenzymatic reaction product (4S,5R)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 4. Copyright (C) 2000 Elsevier Science Ltd.