294198-48-4

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 183625-29-8 methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 

Downstream Products

• 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 
• 294198-65-5 (E)-(4R,5S)-4-Benzyloxy-5-[(R)-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 
• 294198-66-6 (E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester 
• 294198-55-3 (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 
• 294198-67-7 (E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid 
• 294198-56-4 (E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid 
• 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 
• 172923-77-2 (+)-macrosphelide A 
• 459809-89-3 (E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-4-methoxycarbonyl-1-methyl-but-3-enyl 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 
• 459809-62-2 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-2-((E)-(1S,2R)-2-benzyloxy-4-methoxycarbonyl-1-methyl-but-3-enyloxycarbonyl)-1-methyl-ethyl ester 

Relevant academic research and scientific papers

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.

Formal total synthesis of (+)-macrosphelide A based on regioselective hydrolysis using lipase.

Three kinds of seco-macrosphelide A congeners, (4R,5S,10R,11S,15S)-6, (4R,5S,9S,14R,15S)-7 and (3S,8R,9S,14R,15S)-8 were chemically synthesized, and they were exposed to the lipase OF-360 from Candida rugosa to give three hydroxy carboxylic acids, respectively. Macrolactonization of the hydroxy acid (4R,5S,10R,11S)-18 derived from (4R,5S,10R,11S,15S)-6 gave 12-membered lactone (19) in 47% overall yield from 6, while that of the seco-acid (4) derived from (4R,5S,9S,14R,15S)-7 afforded (-)-dibenzyl macrosphelide A (25) in 27% overall yield from 7. Macrolactonization of the hydrolysis product, seco-acid (5) derived from (3S,8R,9S,14R,15S)-8, provided (-)-dibenzyl macrosphelide A (25) (5% overall yield from 8) and 12-membered lactone (19) (20% overall yield from 8) concurrently.