(1R,2R,3S)-3-acetoxy-2-(tert-butyldimethylsilyloxy)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylpropyl acetate

Base Information

Chemical Name:(1R,2R,3S)-3-acetoxy-2-(tert-butyldimethylsilyloxy)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylpropyl acetate
CAS No.:503417-12-7
Molecular Formula:C₂₄H₃₈O₇Si
Molecular Weight:466.647
Hs Code.:

Synonyms:(1R,2R,3S)-3-acetoxy-2-(tert-butyldimethylsilyloxy)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylpropyl acetate

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Chemical Property of (1R,2R,3S)-3-acetoxy-2-(tert-butyldimethylsilyloxy)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylpropyl acetate

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Technology Process of (1R,2R,3S)-3-acetoxy-2-(tert-butyldimethylsilyloxy)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylpropyl acetate

There total 4 articles about (1R,2R,3S)-3-acetoxy-2-(tert-butyldimethylsilyloxy)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylpropyl 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: 83.0%

: 108-24-7
acetic anhydride

: 247042-37-1
(4S)-2,2-dimethyl-4-[(1R,2R,3S)-2-(tert-butyldimethylsilyloxy)-1,3-dihydroxy-3-phenylpropyl]-1,3-dioxolane

: 503417-12-7
(1R,2R,3S)-3-acetoxy-2-(tert-butyldimethylsilyloxy)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylpropyl acetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1016/S0957-4166(02)00638-9

Reference yield:

: 100-52-7
benzaldehyde

: 503417-12-7
(1R,2R,3S)-3-acetoxy-2-(tert-butyldimethylsilyloxy)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylpropyl acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 0.5 h / 0 °C

1.2: diethyl ether / 4 h / 0 °C

2.1: LiBH₄ / diethyl ether; tetrahydrofuran / 2 h / 0 °C

3.1: 83 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 20 °C

With dmap; lithium borohydride; dicyclohexylboron chloride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0957-4166(02)00638-9

Reference yield:

: 115043-29-3
2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone

: 503417-12-7
(1R,2R,3S)-3-acetoxy-2-(tert-butyldimethylsilyloxy)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylpropyl acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 0.5 h / 0 °C

1.2: diethyl ether / 4 h / 0 °C

2.1: LiBH₄ / diethyl ether; tetrahydrofuran / 2 h / 0 °C

3.1: 83 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 20 °C

With dmap; lithium borohydride; dicyclohexylboron chloride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0957-4166(02)00638-9