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

Base Information

Chemical Name:(E)-(4S,5S,6R)-Methyl 4-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-2-enoate
CAS No.:147059-81-2
Molecular Formula:C₁₉H₂₆O₆
Molecular Weight:350.412
Hs Code.:

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

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

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

There total 4 articles about (E)-(4S,5S,6R)-Methyl 4-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-2-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: 96.0%

: 147059-79-8
(E)-(2R,5S,6R)-Methyl 2-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-3-enoate

: 147059-81-2
(E)-(4S,5S,6R)-Methyl 4-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-2-enoate

Guidance literature:: dichloro bis(acetonitrile) palladium(II); In dichloromethane; for 36h; Ambient temperature;
DOI:10.1021/jo00057a008

Reference yield:

: 133323-23-6
(2R,3R)-(E)-3-(Dimethylphenylsilyl)-2-hydroxyhex-4-enoic acid

: 147059-81-2
(E)-(4S,5S,6R)-Methyl 4-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-2-enoate

Guidance literature:: Multi-step reaction with 4 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

4: 96 percent / PdCl₂(CH₃CN)2 / CH₂Cl₂ / 36 h / Ambient temperature

With thionyl chloride; triethylamine; dmap; dichloro bis(acetonitrile) palladium(II); trimethylsilyl trifluoromethanesulfonate; In dichloromethane;
DOI:10.1021/jo00057a008

Reference yield:

: 146962-06-3
(2R,3R)-(E)-Methyl 3-(dimethylphenylsilyl)-2-hydroxyhex-4-enoate

: 147059-81-2
(E)-(4S,5S,6R)-Methyl 4-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-2-enoate

Guidance literature:: Multi-step reaction with 3 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

3: 96 percent / PdCl₂(CH₃CN)2 / CH₂Cl₂ / 36 h / Ambient temperature

With triethylamine; dmap; dichloro bis(acetonitrile) palladium(II); trimethylsilyl trifluoromethanesulfonate; In dichloromethane;
DOI:10.1021/jo00057a008