(1S,2S)-1-(4-benzyloxyphenyl)-3-[4-benzylox-2-(tert-butyldimethylsilyloxy)phenyl]propane-1,2-diol

Base Information

Chemical Name:(1S,2S)-1-(4-benzyloxyphenyl)-3-[4-benzylox-2-(tert-butyldimethylsilyloxy)phenyl]propane-1,2-diol
CAS No.:850816-13-6
Molecular Formula:C₃₅H₄₂O₅Si
Molecular Weight:570.801
Hs Code.:

Synonyms:(1S,2S)-1-(4-benzyloxyphenyl)-3-[4-benzylox-2-(tert-butyldimethylsilyloxy)phenyl]propane-1,2-diol

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Chemical Property of (1S,2S)-1-(4-benzyloxyphenyl)-3-[4-benzylox-2-(tert-butyldimethylsilyloxy)phenyl]propane-1,2-diol

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Technology Process of (1S,2S)-1-(4-benzyloxyphenyl)-3-[4-benzylox-2-(tert-butyldimethylsilyloxy)phenyl]propane-1,2-diol

There total 5 articles about (1S,2S)-1-(4-benzyloxyphenyl)-3-[4-benzylox-2-(tert-butyldimethylsilyloxy)phenyl]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: 88.0%

: (E)-1-(4-benzyloxyphenyl)-3-[4-benzyloxy-2-(tert-butyldimethylsilyloxy)phenyl]propene

: 850816-13-6
(1S,2S)-1-(4-benzyloxyphenyl)-3-[4-benzylox-2-(tert-butyldimethylsilyloxy)phenyl]propane-1,2-diol

Guidance literature:: With methanesulfonamide; AD-mix-α; In chloroform; water; tert-butyl alcohol; at 20 ℃; for 16h; enantioselective reaction;
DOI:10.1055/s-0028-1083361

Reference yield:

: (E)-1-(4-benzyloxyphenyl)-3-(4-benzyloxy-2-hydroxyphenyl)propene

: 850816-13-6
(1S,2S)-1-(4-benzyloxyphenyl)-3-[4-benzylox-2-(tert-butyldimethylsilyloxy)phenyl]propane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / imidazole / dimethylformamide / 20 °C

2: 84 percent / AD-Mix α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 °C

With 1H-imidazole; AD-mix-α; methanesulfonamide; In water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja042727j

Reference yield:

: 4397-53-9
p-benzyloxybenzaldehyde

: 850816-13-6
(1S,2S)-1-(4-benzyloxyphenyl)-3-[4-benzylox-2-(tert-butyldimethylsilyloxy)phenyl]propane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / KOH / methanol / Heating

2.1: Et₃N; ethyl chloroformate / tetrahydrofuran / 1.5 h / 0 °C

2.2: 74 percent / NaBH₄ / H₂O; tetrahydrofuran / 20 °C

3.1: 100 percent / imidazole / dimethylformamide / 20 °C

4.1: 84 percent / AD-Mix α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 °C

With 1H-imidazole; potassium hydroxide; AD-mix-α; methanesulfonamide; chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Claisen-Schmidt reaction / 4.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja042727j