(3S,4R,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyl-4-vinyldecan-4-ol

Base Information

Chemical Name:(3S,4R,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyl-4-vinyldecan-4-ol
CAS No.:110672-02-1
Molecular Formula:C₂₅H₄₀O₄
Molecular Weight:404.59
Hs Code.:

Synonyms:(3S,4R,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyl-4-vinyldecan-4-ol

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Chemical Property of (3S,4R,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyl-4-vinyldecan-4-ol

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Technology Process of (3S,4R,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyl-4-vinyldecan-4-ol

There total 19 articles about (3S,4R,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyl-4-vinyldecan-4-ol 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: 97.0%

: 1826-67-1
vinyl magnesium bromide

: 110653-52-6
(3S,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyldecan-4-one

: 110672-02-1
(3S,4R,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyl-4-vinyldecan-4-ol

Guidance literature:: In tetrahydrofuran; at -40 ℃; for 3h;
DOI:10.1248/cpb.37.1698

Reference yield:

: 81520-10-7
(2S,3S,4S)-5-Benzyloxy-2,4-dimethylpentan-1,3-diol

: 110672-02-1
(3S,4R,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyl-4-vinyldecan-4-ol

Guidance literature:: Multi-step reaction with 6 steps

1: CSA / acetone / 0.5 h / Ambient temperature

2: 96 percent / hydrogen / 10percent Pd/C / ethanol / 3.5 h / Ambient temperature

3: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 30 min, 2) CH₂Cl₂, -70 to 0 deg C

4: 1) NaH / 1) DMF, 45 min, 0 deg C, 2) DMF, THF, 0 to 20 deg C

5: 94 percent / hydrogen / 10percent Pd/C / ethyl acetate

6: 97 percent / tetrahydrofuran / 3 h / -40 °C

With oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; ethyl acetate; acetone;
DOI:10.1248/cpb.37.1698

Reference yield:

: 81470-77-1,98102-72-8,100760-30-3,115181-74-3,133006-91-4,135211-99-3,138124-14-8,145514-09-6
(2S,3R,4S)-1-benzyloxy-3,5-isopropylidenedioxy-2,4-dimethylpentane

: 110672-02-1
(3S,4R,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyl-4-vinyldecan-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / hydrogen / 10percent Pd/C / ethanol / 3.5 h / Ambient temperature

2: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 30 min, 2) CH₂Cl₂, -70 to 0 deg C

3: 1) NaH / 1) DMF, 45 min, 0 deg C, 2) DMF, THF, 0 to 20 deg C

4: 94 percent / hydrogen / 10percent Pd/C / ethyl acetate

5: 97 percent / tetrahydrofuran / 3 h / -40 °C

With oxalyl dichloride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; ethyl acetate;
DOI:10.1248/cpb.37.1698