(4S,5S,6R)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4,5-O-isopropylidene-6-hydroxy-1-heptene

Base Information

Chemical Name:(4S,5S,6R)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4,5-O-isopropylidene-6-hydroxy-1-heptene
CAS No.:925222-13-5
Molecular Formula:C₂₈H₄₀O₄Si
Molecular Weight:468.709
Hs Code.:

Synonyms:(4S,5S,6R)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4,5-O-isopropylidene-6-hydroxy-1-heptene

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Chemical Property of (4S,5S,6R)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4,5-O-isopropylidene-6-hydroxy-1-heptene

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Technology Process of (4S,5S,6R)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4,5-O-isopropylidene-6-hydroxy-1-heptene

There total 3 articles about (4S,5S,6R)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4,5-O-isopropylidene-6-hydroxy-1-heptene 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: 52.0%

: 855282-04-1
(4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene

: 67-64-1
acetone

: 925222-13-5
(4S,5S,6R)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4,5-O-isopropylidene-6-hydroxy-1-heptene

: (4S,5S,6R)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4,5-O-isopropylidene-6-methoxymethoxy-1-heptene

Guidance literature:: With toluene-4-sulfonic acid; for 36h; Heating;
DOI:10.1021/jo0615145

Reference yield:

: 877373-38-1
(2S,3R)-2,3-bis(methoxymethoxy)-4-[(1,1-dimethylethyl)diphenylsilyl]oxybutyraldehyde

: 925222-13-5
(4S,5S,6R)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4,5-O-isopropylidene-6-hydroxy-1-heptene

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / ZnBr₂ / CH₂Cl₂ / 8 h / -78 - 0 °C

2: 52 percent / p-TsOH / 36 h / Heating

With toluene-4-sulfonic acid; zinc dibromide; In dichloromethane;
DOI:10.1021/jo0615145

Reference yield:

: 877373-78-9
(2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-methoxymethoxy-butan-1-ol

: 925222-13-5
(4S,5S,6R)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4,5-O-isopropylidene-6-hydroxy-1-heptene

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / oxalyl chloride; triethylamine; dimethylsulfoxide / CH₂Cl₂ / -78 - 20 °C

2: 90 percent / ZnBr₂ / CH₂Cl₂ / 8 h / -78 - 0 °C

3: 52 percent / p-TsOH / 36 h / Heating

With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; zinc dibromide; In dichloromethane; 1: Swern oxidation;
DOI:10.1021/jo0615145