(1S,2S)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propane-1,2-diol

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Chemical Name:(1S,2S)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propane-1,2-diol
CAS No.:942122-64-7
Molecular Formula:C₅₆H₆₀O₈Si
Molecular Weight:889.173
Hs Code.:
Mol file:942122-64-7.mol

Synonyms:(1S,2S)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propane-1,2-diol

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Chemical Property of (1S,2S)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propane-1,2-diol Edit

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Technology Process of (1S,2S)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propane-1,2-diol

There total 5 articles about (1S,2S)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)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: 82.0%

: 332386-55-7
(E)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propene

: 942122-64-7
(1S,2S)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)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:

: 332386-67-1
ethyl (E)-3,4,5-tris(benzyloxy)cinnamate

: 942122-64-7
(1S,2S)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / DIBAL / tetrahydrofuran; toluene / 2 h / -78 - 20 °C

2: 463 mg / H₂SO₄*SiO₂ / CS₂; CH₂Cl₂ / 3 h / 20 °C

3: 428 mg / imidazole / dimethylformamide / 20 °C

4: AD-mix-α; CH3SO2NH2; H2O / 2-methyl-propan-2-ol; CH2Cl2 / 0 °C

With 1H-imidazole; AD-mix-α; methanesulfonamide; sulfuric acid; water; diisobutylaluminium hydride; In tetrahydrofuran; carbon disulfide; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 4: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol000394z

Reference yield:

: 70424-94-1
methyl 3,4,5-tris(benzyloxy)benzoate

: 942122-64-7
(1S,2S)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propane-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 89 percent / LAH / tetrahydrofuran / 2 h / 20 °C

2.1: PDC / CH₂Cl₂ / 20 °C

2.2: 91 percent / NaH / tetrahydrofuran / 2 h / 20 °C

3.1: 95 percent / DIBAL / tetrahydrofuran; toluene / 2 h / -78 - 20 °C

4.1: 463 mg / H₂SO₄*SiO₂ / CS₂; CH₂Cl₂ / 3 h / 20 °C

5.1: 428 mg / imidazole / dimethylformamide / 20 °C

6.1: AD-mix-α; CH3SO2NH2; H2O / 2-methyl-propan-2-ol; CH2Cl2 / 0 °C

With 1H-imidazole; AD-mix-α; lithium aluminium tetrahydride; dipyridinium dichromate; methanesulfonamide; sulfuric acid; water; diisobutylaluminium hydride; In tetrahydrofuran; carbon disulfide; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 6.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol000394z