(-)-dibenzyl macrosphelide A

Base Information

• Chemical Name: (-)-dibenzyl macrosphelide A
• CAS No.: 294198-57-5
• Molecular Formula: C₃₀H₃₄O₈
• Molecular Weight: 522.595
• Mol file: 294198-57-5.mol

Synonyms:(-)-dibenzyl macrosphelide A

Chemical Property of (-)-dibenzyl macrosphelide A

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (-)-dibenzyl macrosphelide A

There total 22 articles about (-)-dibenzyl macrosphelide A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-2-((E)-(1S,2R)-2-benzyloxy-4-carboxy-1-methyl-but-3-enyloxycarbonyl)-1-methyl-ethyl ester (434938-14-4) → (-)-dibenzyl macrosphelide A (294198-57-5) + (3E,9E)-(5R,6S,11R,12S)-5,11-Bis-benzyloxy-6,12-dimethyl-1,7-dioxa-cyclododeca-3,9-diene-2,8-dione

Guidance literature:

(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-2-((E)-(1S,2R)-2-benzyloxy-4-carboxy-1-methyl-but-3-enyloxycarbonyl)-1-methyl-ethyl ester; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; for 2h;

With dmap; In tetrahydrofuran; toluene; at 100 ℃; for 1h;

DOI:10.3987/com-01-9391

Reference yield: 63.0%

(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-4-((S)-2-carboxy-1-methyl-ethoxycarbonyl)-1-methyl-but-3-enyl ester (434938-13-3) → (-)-dibenzyl macrosphelide A (294198-57-5) + (3E,9E)-(5R,6S,11R,12S)-5,11-Bis-benzyloxy-6,12-dimethyl-1,7-dioxa-cyclododeca-3,9-diene-2,8-dione

Guidance literature:

(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-4-((S)-2-carboxy-1-methyl-ethoxycarbonyl)-1-methyl-but-3-enyl ester; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; for 2h;

With dmap; In tetrahydrofuran; toluene; at 100 ℃; for 12h;

DOI:10.3987/com-01-9391

Reference yield: 27.0%

(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 (459809-62-2) → (-)-dibenzyl macrosphelide A (294198-57-5)

Guidance literature:

(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; With Lipase OF-360; In phosphate buffer; at 35 ℃; for 336h;

With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; toluene; at 20 ℃; for 2h;

With dmap; In tetrahydrofuran; toluene; at 100 ℃; for 12h;

DOI:10.1248/cpb.50.692

upstream raw materials:

(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid

(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-4-((S)-2-carboxy-1-methyl-ethoxycarbonyl)-1-methyl-but-3-enyl ester

(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-2-((E)-(1S,2R)-2-benzyloxy-4-carboxy-1-methyl-but-3-enyloxycarbonyl)-1-methyl-ethyl ester

(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

Downstream raw materials:

(+)-macrosphelide A