(2S,3S,5S,6R)-6-(tert-butyldimethylsilyloxy)-3-<(tert-butyldiphenylsilyloxy)methyl>-2-hydroxy-5-methyl-2-<1-methylene-3-(phenylsulphonyl)propyl>cyclohexanone

Base Information

Chemical Name:(2S,3S,5S,6R)-6-(tert-butyldimethylsilyloxy)-3-<(tert-butyldiphenylsilyloxy)methyl>-2-hydroxy-5-methyl-2-<1-methylene-3-(phenylsulphonyl)propyl>cyclohexanone
CAS No.:135419-76-0
Molecular Formula:C₄₀H₅₆O₆SSi₂
Molecular Weight:721.118
Hs Code.:

(2S,3S,5S,6R)-6-(tert-butyldimethylsilyloxy)-3-<(tert-butyldiphenylsilyloxy)methyl>-2-hydroxy-5-methyl-2-<1-methylene-3-(phenylsulphonyl)propyl>cyclohexanone

Synonyms:(2S,3S,5S,6R)-6-(tert-butyldimethylsilyloxy)-3-<(tert-butyldiphenylsilyloxy)methyl>-2-hydroxy-5-methyl-2-<1-methylene-3-(phenylsulphonyl)propyl>cyclohexanone

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Chemical Property of (2S,3S,5S,6R)-6-(tert-butyldimethylsilyloxy)-3-<(tert-butyldiphenylsilyloxy)methyl>-2-hydroxy-5-methyl-2-<1-methylene-3-(phenylsulphonyl)propyl>cyclohexanone

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Technology Process of (2S,3S,5S,6R)-6-(tert-butyldimethylsilyloxy)-3-<(tert-butyldiphenylsilyloxy)methyl>-2-hydroxy-5-methyl-2-<1-methylene-3-(phenylsulphonyl)propyl>cyclohexanone

There total 12 articles about (2S,3S,5S,6R)-6-(tert-butyldimethylsilyloxy)-3-<(tert-butyldiphenylsilyloxy)methyl>-2-hydroxy-5-methyl-2-<1-methylene-3-(phenylsulphonyl)propyl>cyclohexanone 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:

: 127785-52-8
2-bromo-4-phenylthiobut-1-ene

: 135419-76-0
(2S,3S,5S,6R)-6-(tert-butyldimethylsilyloxy)-3-<(tert-butyldiphenylsilyloxy)methyl>-2-hydroxy-5-methyl-2-<1-methylene-3-(phenylsulphonyl)propyl>cyclohexanone

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) tert-BuLi / 1.) pentane, ether, THF, -78 deg C, 5 min, 2.) -78 deg C, 5 min

2: 89 percent / oxone, pH 4 aqueous buffer / tetrahydrofuran; methanol / 2 h / Ambient temperature

3: 69 percent / tert-butyl hydroperoxide, vanadyl acetylacetonate / toluene; CH₂Cl₂ / Ambient temperature; 0 deg C to RT

4: 80 percent / 15percent aq. H₂SO₄ / tetrahydrofuran / 12 h / 60 °C

5: 91 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

6: 86 percent / NEt₃ / CH₂Cl₂ / 0.25 h / Ambient temperature

7: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) THF, -35 deg C, 20 min, 2.) -78 deg C -> RT

With 1H-imidazole; tert.-butylhydroperoxide; Oxone; oxalyl dichloride; pH 4 aqueous buffer; vanadyl acetylacetonate; sulfuric acid; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 135419-76-0
(2S,3S,5S,6R)-6-(tert-butyldimethylsilyloxy)-3-<(tert-butyldiphenylsilyloxy)methyl>-2-hydroxy-5-methyl-2-<1-methylene-3-(phenylsulphonyl)propyl>cyclohexanone

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / NEt₃ / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) THF, -35 deg C, 20 min, 2.) -78 deg C -> RT

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;

Reference yield:

: 131414-03-4
(4S,6S)-6-<(tert-butyldiphenylsilyloxy)methyl>-4-methylcyclohex-2-enone

: 135419-76-0
(2S,3S,5S,6R)-6-(tert-butyldimethylsilyloxy)-3-<(tert-butyldiphenylsilyloxy)methyl>-2-hydroxy-5-methyl-2-<1-methylene-3-(phenylsulphonyl)propyl>cyclohexanone

Guidance literature:: Multi-step reaction with 7 steps

1: 64 percent / dimethyldioxirane / acetone; CH₂Cl₂ / 40 h / Ambient temperature

2: 1.) tert-BuLi / 1.) pentane, THF, -78 deg C, 10 min, 2.) -78 deg C, 10 min

3: 88 percent / oxone, pH 4 aqueous buffer / tetrahydrofuran; methanol / 3.5 h / Ambient temperature

4: 80 percent / 15percent aq. H₂SO₄ / tetrahydrofuran / 12 h / 60 °C

5: 91 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

6: 86 percent / NEt₃ / CH₂Cl₂ / 0.25 h / Ambient temperature

7: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) THF, -35 deg C, 20 min, 2.) -78 deg C -> RT

With 1H-imidazole; Oxone; oxalyl dichloride; pH 4 aqueous buffer; sulfuric acid; tert.-butyl lithium; 3,3-dimethyldioxirane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;