(1S,2R,5R,6S)-5,6-bis-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-3-methylcyclohex-3-enol

Base Information

Chemical Name:(1S,2R,5R,6S)-5,6-bis-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-3-methylcyclohex-3-enol
CAS No.:403986-36-7
Molecular Formula:C₃₅H₅₈O₄Si₃
Molecular Weight:627.1
Hs Code.:

Synonyms:(1S,2R,5R,6S)-5,6-bis-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-3-methylcyclohex-3-enol

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Chemical Property of (1S,2R,5R,6S)-5,6-bis-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-3-methylcyclohex-3-enol

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Technology Process of (1S,2R,5R,6S)-5,6-bis-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-3-methylcyclohex-3-enol

There total 4 articles about (1S,2R,5R,6S)-5,6-bis-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-3-methylcyclohex-3-enol 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: 58.0%

: 403986-34-5
(1S,2R,3R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-methylcyclohex-4-ene-1,2,3-triol

: 69739-34-0
t-butyldimethylsiyl triflate

: 403986-36-7
(1S,2R,5R,6S)-5,6-bis-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-3-methylcyclohex-3-enol

Guidance literature:: With triethylamine; In dichloromethane; at 18 ℃; for 1h;
DOI:10.1039/b106419c

Reference yield:

: 41977-20-2
(2R,3S)-2,3-dihydroxy-1-methylcyclohexa-4,6-diene

: 403986-36-7
(1S,2R,5R,6S)-5,6-bis-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-3-methylcyclohex-3-enol

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / imidazole / CH₂Cl₂ / 1.5 h / 18 °C

2: 7 percent / osmium tetroxide; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; acetone; H₂O / 1 h / 60 °C

3: 58 percent / Et₃N / CH₂Cl₂ / 1 h / 18 °C

With 1H-imidazole; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; water; acetone; tert-butyl alcohol; 2: UpJohn oxidation;
DOI:10.1039/b106419c

Reference yield:

: 124647-14-9
(1S-cis)-6-t-butyldiphenylsilyloxy-5-methyl-2,4-cyclohexadien-1-ol

: 403986-36-7
(1S,2R,5R,6S)-5,6-bis-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-3-methylcyclohex-3-enol

Guidance literature:: Multi-step reaction with 2 steps

1: 7 percent / osmium tetroxide; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; acetone; H₂O / 1 h / 60 °C

2: 58 percent / Et₃N / CH₂Cl₂ / 1 h / 18 °C

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; water; acetone; tert-butyl alcohol; 1: UpJohn oxidation;
DOI:10.1039/b106419c