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

Base Information

Chemical Name:(+)-(4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methylcyclohex-2-enone
CAS No.:887404-74-2
Molecular Formula:C₁₃H₂₄O₄Si
Molecular Weight:272.417
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

There total 4 articles about (+)-(4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methylcyclohex-2-enone 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:

: (2R,4S,5S,6R)-2-Benzenesulfinyl-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-cyclohexanone

: 887404-74-2
(+)-(4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methylcyclohex-2-enone

Guidance literature:: (2R,4S,5S,6R)-2-Benzenesulfinyl-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-2-methyl-cyclohexanone; In chloroform; for 2h; Heating;

With trifluoroacetic acid; In chloroform; at 20 ℃; for 3h;
DOI:10.1021/ol060173e

Reference yield:

: (4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-phenylsulfanyl-cyclohex-2-enone

: 887404-74-2
(+)-(4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 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

3.1: MCPBA / CHCl₃ / 1 h / 0 °C

4.1: CHCl₃ / 2 h / Heating

4.2: TFA / CHCl₃ / 3 h / 20 °C

With potassium tert-butylate; water; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; osmium(VIII) oxide; In tetrahydrofuran; chloroform; acetone; tert-butyl alcohol;
DOI:10.1021/ol060173e

Reference yield:

: 887404-60-6
(4S,6R)-4-(tert-butyldimethylsilyloxy)-6-methyl-6-phenylthiocyclohex-2-enone

: 887404-74-2
(+)-(4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-5,6-dihydroxy-2-methylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: MCPBA / CHCl₃ / 1 h / 0 °C

3.1: CHCl₃ / 2 h / Heating

3.2: TFA / CHCl₃ / 3 h / 20 °C

With water; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; osmium(VIII) oxide; In chloroform; acetone; tert-butyl alcohol;
DOI:10.1021/ol060173e