(2S,4S,5S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yn-2-ol

Base Information

Chemical Name:(2S,4S,5S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yn-2-ol
CAS No.:268736-78-3
Molecular Formula:C₂₄H₄₀O₄Si
Molecular Weight:420.665
Hs Code.:

Synonyms:(2S,4S,5S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yn-2-ol

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Chemical Property of (2S,4S,5S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yn-2-ol

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Technology Process of (2S,4S,5S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yn-2-ol

There total 1 articles about (2S,4S,5S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yn-2-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: 85.0%

: 100-39-0
benzyl bromide

: (4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yne-1,2-diol

: 268736-78-3
(2S,4S,5S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yn-2-ol

Guidance literature:: (4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yne-1,2-diol; With di(n-butyl)tin oxide; In toluene; at 110 ℃; for 12h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In toluene; at 80 ℃; for 2h; Further stages.;
DOI:10.1039/b000424n

Reference yield: 97.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 268736-78-3
(2S,4S,5S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yn-2-ol

: 1053634-23-3
[(2S,4S,5S)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-ynyloxymethyl]-benzene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 25 ℃;
DOI:10.1039/b000424n

Reference yield:

: 268736-78-3
(2S,4S,5S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-dec-8-yn-2-ol

: (3E,5E,7E,11E,13E)-(9R,10R,17S,18S,20S)-20-Benzyloxymethyl-10,17-dihydroxy-18-methoxy-3,5,7,9,13-pentamethyl-oxacycloicosa-3,5,7,11,13-pentaen-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / 2,6-Lutidine / CH₂Cl₂ / 0 - 25 °C

2.1: Cp₂ZrHCl / tetrahydrofuran / 2 h / 50 °C

2.2: I₂ / tetrahydrofuran / 0.5 h / -15 - 25 °C

3.1: Bu₃Sn / PdCl₂(PPh₃)2 / tetrahydrofuran / 0.5 h / 0 °C

3.2: 60 percent / Pd(CH₃CN)2Cl₂ / dimethylformamide / 48 h / 25 °C

4.1: 80 percent / TBAF / tetrahydrofuran / 12 h / 25 °C

5.1: 2,4,6-Trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 1.5 h / 0 °C

5.2: 60 percent / 4-DMAP / benzene; tetrahydrofuran / 1 h / 25 °C

With 2,6-dimethylpyridine; Schwartz's reagent; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; 1.1: Etherification / 2.1: Metallation / 2.2: Iodination / 3.1: Addition / 3.2: Alkylation / 4.1: Desilylation / 5.1: Substitution / 5.2: Esterification;
DOI:10.1039/b000424n