(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

Base Information

• Chemical Name: (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
• CAS No.: 434938-14-4
• Molecular Formula: C₃₀H₃₆O₉
• Molecular Weight: 540.61
• Mol file: 434938-14-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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: 96.0%

(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 (434938-27-9) → (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)

Guidance literature:

With sodium acetate; acetic acid; zinc; In tetrahydrofuran; at 20 ℃; for 3.5h;

DOI:10.3987/com-01-9391

Reference yield:

(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) → (-)-(4R,5S)-4-benzyloxy-5-hydroxy-(2E)-hexenoic acid (459809-85-9) + (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)

Guidance literature:

With Lipase OF-360; In phosphate buffer; at 35 ℃; for 336h; Title compound not separated from byproducts;

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-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)

Guidance literature:

Multi-step reaction with 5 steps

1.1: imidazole / dimethylformamide

2.1: aq. NaOH / methanol

2.2: 2M HCl

3.1: 53 percent / dicyclohexylcarbodiimide; 2-(dimethylamino)pyridine; (+)-camphorsulfonic acid / CH₂Cl₂ / 48 h / 20 °C

4.1: 56 percent / AcOH; H₂O / tetrahydrofuran / 12 h / 80 °C

5.1: lipase OF-360 / aq. phosphate buffer / 336 h / 35 °C

With 1H-imidazole; 2-(Dimethylamino)pyridine; sodium hydroxide; Lipase OF-360; water; acetic acid; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.50.692

upstream raw materials:

(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

(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

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

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

Downstream raw materials:

(-)-dibenzyl macrosphelide A