(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hex-1-yl acetate

Base Information

Chemical Name:(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hex-1-yl acetate
CAS No.:1053738-86-5
Molecular Formula:C₂₇H₅₀O₅Si₂
Molecular Weight:510.862
Hs Code.:

Synonyms:(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hex-1-yl acetate

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Chemical Property of (2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hex-1-yl acetate

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Technology Process of (2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hex-1-yl acetate

There total 9 articles about (2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hex-1-yl acetate 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: 91.0%

: 108-24-7
acetic anhydride

: 250346-42-0
(2S,3R,5R)-5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexan-1-ol

: 1053738-86-5
(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hex-1-yl acetate

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1039/a909243i

Reference yield:

: 19810-31-2
Benzyloxyacetyl chloride

: 1053738-86-5
(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hex-1-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran / 1.5 h / -78 - -20 °C

1.2: 84 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: Sn(OTf)2; NEt₃ / CH₂Cl₂ / 1 h / -78 °C

2.2: 60 percent / TMEDA / CH₂Cl₂ / 2 h / -78 °C

3.1: 84 percent / imidazole / dimethylformamide / 0 - 20 °C

4.1: 82 percent / LiBH₄ / tetrahydrofuran / 5 h / 0 - 20 °C

5.1: 91 percent / NEt₃ / CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; lithium borohydride; tin(II) trifluoromethanesulfonate; n-butyllithium; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Acylation / 2.1: Metallation / 2.2: Aldol reaction / 3.1: Etherification / 4.1: Reduction / 5.1: Acetylation;
DOI:10.1039/a909243i

Reference yield:

: 109715-46-0
ethyl (R)-3-[(tert-butyldimethylsilyl)oxy]butanoate

: 1053738-86-5
(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hex-1-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 89 percent / LiBH₄ / diethyl ether; methanol / 5 h / Heating

2.1: 81 percent / NMO; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 4 h / 20 °C

3.1: Sn(OTf)2; NEt₃ / CH₂Cl₂ / 1 h / -78 °C

3.2: 60 percent / TMEDA / CH₂Cl₂ / 2 h / -78 °C

4.1: 84 percent / imidazole / dimethylformamide / 0 - 20 °C

5.1: 82 percent / LiBH₄ / tetrahydrofuran / 5 h / 0 - 20 °C

6.1: 91 percent / NEt₃ / CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; lithium borohydride; tin(II) trifluoromethanesulfonate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Oxidation / 3.1: Metallation / 3.2: Aldol reaction / 4.1: Etherification / 5.1: Reduction / 6.1: Acetylation;
DOI:10.1039/a909243i