(1S,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate

Base Information

Chemical Name:(1S,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate
CAS No.:677300-62-8
Molecular Formula:C₂₇H₅₀O₆Si₂
Molecular Weight:526.861
Hs Code.:

Synonyms:(1S,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate

Chemical Property:

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Technology Process of (1S,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate

There total 5 articles about (1S,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate 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:

: (1S)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-4-hydroxy-5-methyl-2-oxohexyl benzoate

: 677300-62-8
(1S,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate

: (1S)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate

Guidance literature:: With lithium borohydride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h;
DOI:10.1021/jo0356356

Reference yield:

: 98-88-4
benzoyl chloride

: 677300-62-8
(1S,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

2.1: (Cyclohexyl)2BCl; Et₃N / diethyl ether / 1 h / 0 °C

2.2: diethyl ether / 5 h / -78 °C

3.1: tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / 18 h / -30 °C

With dmap; dicyclohexylboron chloride; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo0356356

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 677300-62-8
(1S,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-2,4-dihydroxy-5-methylhexyl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 70 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

3.1: (Cyclohexyl)2BCl; Et₃N / diethyl ether / 1 h / 0 °C

3.2: diethyl ether / 5 h / -78 °C

4.1: tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / 18 h / -30 °C

With 1H-imidazole; dmap; dicyclohexylboron chloride; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo0356356