(2R,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methyl-2-phenythiocyclohexanone

Base Information

• Chemical Name: (2R,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methyl-2-phenythiocyclohexanone
• CAS No.: 887404-67-3
• Molecular Formula: C₁₉H₃₀O₄SSi
• Molecular Weight: 382.596

Synonyms:(2R,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methyl-2-phenythiocyclohexanone

Chemical Property of (2R,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methyl-2-phenythiocyclohexanone

Chemical Property:

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Technology Process of (2R,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methyl-2-phenythiocyclohexanone

There total 1 articles about (2R,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methyl-2-phenythiocyclohexanone 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:

(4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-phenylsulfanyl-cyclohex-2-enone → (2R,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methyl-2-phenythiocyclohexanone (887404-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butoxide / tetrahydrofuran / 0.25 h / -78 °C

1.2: tetrahydrofuran / 2 h / 20 °C

2.1: N-methylmorpholine N-oxide; water / osmium tetroxide / acetone; 2-methyl-propan-2-ol / 4 h / 20 °C

With potassium tert-butylate; water; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; acetone; tert-butyl alcohol;

DOI:10.1021/ol060173e

Reference yield:

(2R,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methyl-2-phenythiocyclohexanone (887404-67-3) → (2R,4S,5S,6R)-2-Benzenesulfinyl-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-cyclohexanone

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 ℃; for 1h;

DOI:10.1021/ol060173e

Reference yield:

(2R,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methyl-2-phenythiocyclohexanone (887404-67-3) → (+)-(2R,3S,4S,6S)-4-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-6-methylcyclohexanone (887404-70-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 4h; Heating;

DOI:10.1021/ol060173e

Downstream raw materials:

(+)-(2R,3S,4S,6S)-4-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-6-methylcyclohexanone

(+)-(4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methylcyclohex-2-enone

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