(E)-(2R,5S,6R)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate

Base Information

• Chemical Name: (E)-(2R,5S,6R)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate
• CAS No.: 147059-79-8
• Molecular Formula: C₁₉H₂₆O₆
• Molecular Weight: 350.412
• Mol file: 147059-79-8.mol

Synonyms:(E)-(2R,5S,6R)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate

Chemical Property of (E)-(2R,5S,6R)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2R,5S,6R)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate

There total 3 articles about (E)-(2R,5S,6R)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate 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:

(2R,3R)-(E)-3-(Dimethylphenylsilyl)-2-hydroxyhex-4-enoic acid (133323-23-6) → (E)-(2R,5S,6R)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate (147059-79-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / SOCl₂ / 3 h / 0 deg C to r.t.

2: 85 percent / Et₃N / DMAP / CH₂Cl₂ / Ambient temperature

3: trimethylsilyl trifluoromethanesulfonate (TMSOTf) / CH₂Cl₂ / a) -78 deg C to -25 deg C, b) -25 deg C

With thionyl chloride; triethylamine; dmap; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1021/jo00057a008

Reference yield:

(2R,3R)-(E)-Methyl 3-(dimethylphenylsilyl)-2-hydroxyhex-4-enoate (146962-06-3) → (E)-(2R,5S,6R)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate (147059-79-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Et₃N / DMAP / CH₂Cl₂ / Ambient temperature

2: trimethylsilyl trifluoromethanesulfonate (TMSOTf) / CH₂Cl₂ / a) -78 deg C to -25 deg C, b) -25 deg C

With triethylamine; dmap; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1021/jo00057a008

Reference yield:

2-benzyloxy-1,1-dimethoxyethane (127657-97-0) + (2R,3R)-(E)-Methyl 2-acetoxy-3-(dimethylphenylsilyl)-hex-4-enoate (143446-41-7) → (E)-(2R,5S,6S)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate + (E)-(2R,5S,6R)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate (147059-79-8)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; Yield given. Yields of byproduct given. Title compound not separated from byproducts; a) -78 deg C to -25 deg C, b) -25 deg C;

DOI:10.1021/jo00057a008

upstream raw materials:

2-benzyloxy-1,1-dimethoxyethane

(2R,3R)-(E)-Methyl 2-acetoxy-3-(dimethylphenylsilyl)-hex-4-enoate

(2R,3R)-(E)-3-(Dimethylphenylsilyl)-2-hydroxyhex-4-enoic acid

(2R,3R)-(E)-Methyl 3-(dimethylphenylsilyl)-2-hydroxyhex-4-enoate

Downstream raw materials:

(E)-(4S,5S,6R)-Methyl 4-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-2-enoate

Refernces