(1R,2R,3R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol

Base Information

Chemical Name:(1R,2R,3R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol
CAS No.:130009-52-8
Molecular Formula:C₂₁H₃₆O₄Si
Molecular Weight:380.6
Hs Code.:

Synonyms:(1R,2R,3R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol

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Chemical Property of (1R,2R,3R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol

Chemical Property:

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Technology Process of (1R,2R,3R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol

There total 9 articles about (1R,2R,3R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol 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: 78.0%

: 130009-51-7
(1R,2R,3R,6R)-3-Benzyloxy-6-hydroxymethyl-2-methoxy-cyclohexanol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 130009-52-8
(1R,2R,3R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1016/S0040-4039(00)89010-3

Reference yield:

: 129952-17-6
(E)-(2R,3R)-2-Methoxy-8-trimethylsilanyl-oct-6-ene-1,3-diol

: 130009-52-8
(1R,2R,3R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

2: 73 percent / NaH / dimethylformamide / 18 h / 0 to 20 deg C

3: 84 percent / pyridinium p-toluenesulfonate / methanol / 3.5 h / 50 °C

4: DMSO, (COCl)2, NEt₃ / CH₂Cl₂ / 1 h / -60 °C

5: BF₃-Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

6: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) H₂O, MeOH, 0 to 40 deg C, 3 h

7: 78 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)89010-3

Reference yield:

: 129952-16-5
(E)-(2S,3R)-3-Hydroxy-2-methoxy-8-trimethylsilanyl-oct-6-enoic acid methyl ester

: 130009-52-8
(1R,2R,3R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol

Guidance literature:: Multi-step reaction with 8 steps

1: 84 percent / LiAlH₄ / diethyl ether / 3 h / 0 to 20 deg C

2: 96 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

3: 73 percent / NaH / dimethylformamide / 18 h / 0 to 20 deg C

4: 84 percent / pyridinium p-toluenesulfonate / methanol / 3.5 h / 50 °C

5: DMSO, (COCl)2, NEt₃ / CH₂Cl₂ / 1 h / -60 °C

6: BF₃-Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

7: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) H₂O, MeOH, 0 to 40 deg C, 3 h

8: 78 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)89010-3