[(3S,4S)-3-benzyloxy-4-ethynyloxy-7,7-dimethoxy-heptyloxy]-tert-butyldimethylsilane

Base Information

Chemical Name:[(3S,4S)-3-benzyloxy-4-ethynyloxy-7,7-dimethoxy-heptyloxy]-tert-butyldimethylsilane
CAS No.:910057-85-1
Molecular Formula:C₂₄H₄₀O₅Si
Molecular Weight:436.664
Hs Code.:

Synonyms:[(3S,4S)-3-benzyloxy-4-ethynyloxy-7,7-dimethoxy-heptyloxy]-tert-butyldimethylsilane

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Chemical Property of [(3S,4S)-3-benzyloxy-4-ethynyloxy-7,7-dimethoxy-heptyloxy]-tert-butyldimethylsilane

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Technology Process of [(3S,4S)-3-benzyloxy-4-ethynyloxy-7,7-dimethoxy-heptyloxy]-tert-butyldimethylsilane

There total 5 articles about [(3S,4S)-3-benzyloxy-4-ethynyloxy-7,7-dimethoxy-heptyloxy]-tert-butyldimethylsilane 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: 72.0%

: 910057-97-5
(4S,5S)-5-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethoxy-heptan-4-ol

: 79-01-6
Trichloroethylene

: 910057-85-1
[(3S,4S)-3-benzyloxy-4-ethynyloxy-7,7-dimethoxy-heptyloxy]-tert-butyldimethylsilane

Guidance literature:: (4S,5S)-5-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethoxy-heptan-4-ol; Trichloroethylene; With potassium hydride; In tetrahydrofuran; at -78 - 20 ℃;

With methyllithium; In tetrahydrofuran; diethyl ether; at -78 - -40 ℃; for 1.5h;
DOI:10.1021/ol0614471

Reference yield:

: 910057-84-0
(S)-3-Benzyloxy-tetrahydro-furan-2-ol

: 910057-85-1
[(3S,4S)-3-benzyloxy-4-ethynyloxy-7,7-dimethoxy-heptyloxy]-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 82 percent / MgBr₂*Et₂O; 1,2-dibromoethane / diethyl ether; CH₂Cl₂; tetrahydrofuran / 24 h / 20 °C

2.1: 93 percent / imidazole / CH₂Cl₂; toluene / 1 h / 20 °C

3.1: KH / tetrahydrofuran / -78 - 20 °C

3.2: 72 percent / MeLi / tetrahydrofuran; diethyl ether / 1.5 h / -78 - -40 °C

With 1H-imidazole; potassium hydride; ethylene dibromide; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol0614471

Reference yield:

: 910057-96-4
(3S,4S)-3-Benzyloxy-7,7-dimethoxy-heptane-1,4-diol

: 910057-85-1
[(3S,4S)-3-benzyloxy-4-ethynyloxy-7,7-dimethoxy-heptyloxy]-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / imidazole / CH₂Cl₂; toluene / 1 h / 20 °C

2.1: KH / tetrahydrofuran / -78 - 20 °C

2.2: 72 percent / MeLi / tetrahydrofuran; diethyl ether / 1.5 h / -78 - -40 °C

With 1H-imidazole; potassium hydride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ol0614471