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

Base Information

• Chemical Name: methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-bis<(methylsulfonyl)oxy>-2-methyl-2-heptenoate
• CAS No.: 114659-37-9
• Molecular Formula: C₂₅H₃₂O₁₀S₂
• Molecular Weight: 556.655

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

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

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

There total 2 articles about methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-bis<(methylsulfonyl)oxy>-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: 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:

D-(+)-xylose 3,5-bis(benzyl ether) (16054-77-6,120693-82-5,120693-83-6) → methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-bis<(methylsulfonyl)oxy>-2-methyl-2-heptenoate (114659-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / CH₂Cl₂ / 5 h / Ambient temperature

2: 94 percent / pyridine / CH₂Cl₂ / 10 h / 0 °C

With pyridine; In dichloromethane;

DOI:10.1021/jo00278a015

Reference yield: 99.0%

lithium cyano n-butyl cuprate (41742-63-6) + methyl (4S,5R,6R,2E)-5,7-bis(benzyloxy)-4,6-bis<(methylsulfonyl)oxy>-2-methyl-2-heptenoate (114659-37-9) → methyl (5R,6R,2S,3E)-5,7-bis(benzyloxy)-2-butyl-6-<(methylsulfonyl)oxy>-2-methyl-3-heptenoate (114659-39-1)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃; for 0.166667h;

DOI:10.1039/c39870001596

upstream raw materials:

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

methanesulfonyl chloride

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

Downstream raw materials:

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

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

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