methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-dihydroxy-2-methyl-2-heptenoate

Base Information

• Chemical Name: methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-dihydroxy-2-methyl-2-heptenoate
• CAS No.: 122539-37-1
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.472
• Mol file: 122539-37-1.mol

Synonyms:methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-dihydroxy-2-methyl-2-heptenoate

Chemical Property of methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-dihydroxy-2-methyl-2-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-dihydroxy-2-methyl-2-heptenoate

There total 1 articles about methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-dihydroxy-2-methyl-2-heptenoate 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: 82.0%

D-(+)-xylose 3,5-bis(benzyl ether) (16054-77-6,120693-82-5,120693-83-6) + methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7) → methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-dihydroxy-2-methyl-2-heptenoate (122539-37-1)

Guidance literature:

In dichloromethane; for 5h; Ambient temperature;

DOI:10.1021/jo00278a015

Reference yield: 94.0%

methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-dihydroxy-2-methyl-2-heptenoate (122539-37-1) + methanesulfonyl chloride (124-63-0) → methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-bis<(methylsulfonyl)oxy>-2-methyl-2-heptenoate (114659-37-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 10h;

DOI:10.1021/jo00278a015

Reference yield:

methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-dihydroxy-2-methyl-2-heptenoate (122539-37-1) → methyl (5R,6R,2S,3E)-5,7-bis(benzyloxy)-6-<(methylsulfonyl)oxy>-2-methyl-2-propyl-3-heptenoate (114659-38-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / CH₂Cl₂ / 10 h / 0 °C

2: 91 percent / tetrahydrofuran / 0.5 h / -78 °C

With pyridine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00278a015

upstream raw materials:

D-(+)-xylose 3,5-bis(benzyl ether)

methyl 2-(triphenylphosphoranylidene)propionate

Downstream raw materials:

methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-bis<(methylsulfonyl)oxy>-2-methyl-2-heptenoate

methyl (5R,6R,2S,3E)-5,7-bis(benzyloxy)-6-<(methylsulfonyl)oxy>-2-methyl-2-propyl-3-heptenoate

methyl (5R,6R,2S,3E)-5,7-bis(benzyloxy)-2-butyl-6-<(methylsulfonyl)oxy>-2-methyl-3-heptenoate