(E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester
• CAS No.: 459809-71-3
• Molecular Formula: C₁₈H₂₄O₆
• Molecular Weight: 336.385
• Mol file: 459809-71-3.mol

Synonyms:(E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester

Chemical Property of (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester

There total 2 articles about (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester 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: 69.0%

(E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid methyl ester (459809-78-0) → (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester (459809-71-3)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 80 ℃; for 24h;

DOI:10.1248/cpb.50.692

Reference yield:

methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate (183625-29-8) → (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester (459809-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine; (+)-camphorsulfonic acid / CH₂Cl₂ / 48 h / 20 °C

2: 69 percent / AcOH; H₂O / tetrahydrofuran / 24 h / 80 °C

With dmap; water; acetic acid; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.50.692

Reference yield: 53.0%

(4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid (294198-49-5) + (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester (459809-71-3) → (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 (459809-90-6)

Guidance literature:

With 2-(Dimethylamino)pyridine; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1248/cpb.50.692

upstream raw materials:

(E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid methyl ester

methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate

Downstream raw materials:

(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

(-)-(4R,5S)-4-benzyloxy-5-hydroxy-(2E)-hexenoic acid

(-)-dibenzyl macrosphelide A

(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