(1S,2S)-3-[2-benzyloxy-6-(tert-butyl-dimethylsilanyloxy)-4-methoxymethoxyphenyl]-1-(4-benzyloxy-3-methoxyphenyl)propane-1,2-diol

Base Information

Chemical Name:(1S,2S)-3-[2-benzyloxy-6-(tert-butyl-dimethylsilanyloxy)-4-methoxymethoxyphenyl]-1-(4-benzyloxy-3-methoxyphenyl)propane-1,2-diol
CAS No.:1365537-53-6
Molecular Formula:C₃₈H₄₈O₈Si
Molecular Weight:660.88
Hs Code.:

Synonyms:(1S,2S)-3-[2-benzyloxy-6-(tert-butyl-dimethylsilanyloxy)-4-methoxymethoxyphenyl]-1-(4-benzyloxy-3-methoxyphenyl)propane-1,2-diol

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Chemical Property of (1S,2S)-3-[2-benzyloxy-6-(tert-butyl-dimethylsilanyloxy)-4-methoxymethoxyphenyl]-1-(4-benzyloxy-3-methoxyphenyl)propane-1,2-diol

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Technology Process of (1S,2S)-3-[2-benzyloxy-6-(tert-butyl-dimethylsilanyloxy)-4-methoxymethoxyphenyl]-1-(4-benzyloxy-3-methoxyphenyl)propane-1,2-diol

There total 11 articles about (1S,2S)-3-[2-benzyloxy-6-(tert-butyl-dimethylsilanyloxy)-4-methoxymethoxyphenyl]-1-(4-benzyloxy-3-methoxyphenyl)propane-1,2-diol 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:

: 1429227-36-0
(E)-{3-benzyloxy-2-[3-(4-benzyloxy-3-methoxyphenyl)allyl]-5-methoxymethoxyphenoxy}tert-butyldimethylsilane

: 1365537-53-6
(1S,2S)-3-[2-benzyloxy-6-(tert-butyl-dimethylsilanyloxy)-4-methoxymethoxyphenyl]-1-(4-benzyloxy-3-methoxyphenyl)propane-1,2-diol

: (1R,2R)-3-[2-benzyloxy-6-(tert-butyl-dimethylsilanyloxy)-4-methoxymethoxyphenyl]-1-(4-benzyloxy-3-methoxyphenyl)propane-1,2-diol

Guidance literature:: With methanesulfonamide; AD-mix-α; In tetrahydrofuran; water; tert-butyl alcohol; at -1 ℃; for 96h; Overall yield = 93 %; Overall yield = 9.28 g; enantioselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2013.02.012

Reference yield:

: 1365537-40-1
C₃₂H₃₀O₇

: 1365537-53-6
(1S,2S)-3-[2-benzyloxy-6-(tert-butyl-dimethylsilanyloxy)-4-methoxymethoxyphenyl]-1-(4-benzyloxy-3-methoxyphenyl)propane-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran; ethanol / 5.08 h / -40 - 0 °C

2: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

3: AD-mix-α; methanesulfonamide; water / tetrahydrofuran; tert-butyl alcohol / 16 h / 0 - 20 °C

With 1H-imidazole; sodium tetrahydroborate; methanesulfonamide; cerium(III) chloride heptahydrate; AD-mix-α; water; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Sharpless dihydroxylation;
DOI:10.1016/j.tetlet.2012.01.054

Reference yield:

: 1365536-83-9
1-(2-(benzyloxy)-6-hydroxy-4-(methoxymethoxy)phenyl)ethan-1-one

: 1365537-53-6
(1S,2S)-3-[2-benzyloxy-6-(tert-butyl-dimethylsilanyloxy)-4-methoxymethoxyphenyl]-1-(4-benzyloxy-3-methoxyphenyl)propane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

1.2: 1.08 h / 0 - 20 °C

1.3: 0 °C

2.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran; ethanol / 5.08 h / -40 - 0 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

4.1: AD-mix-α; methanesulfonamide; water / tetrahydrofuran; tert-butyl alcohol / 16 h / 0 - 20 °C

With 1H-imidazole; sodium tetrahydroborate; methanesulfonamide; cerium(III) chloride heptahydrate; AD-mix-α; water; sodium hydride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol; 4.1: Sharpless dihydroxylation;
DOI:10.1016/j.tetlet.2012.01.054