(2S,3S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-ol

Base Information

Chemical Name:(2S,3S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-ol
CAS No.:475976-12-6
Molecular Formula:C₂₀H₃₃NO₅SSi
Molecular Weight:427.637
Hs Code.:

Synonyms:(2S,3S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-ol

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Chemical Property of (2S,3S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-ol

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Technology Process of (2S,3S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-ol

There total 7 articles about (2S,3S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-ol 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: 89.0%

: 475976-11-5
(2S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,6-dihydro-2H-pyridin-3-one

: 475976-12-6
(2S,3S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-ol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -30 ℃; for 0.666667h;
DOI:10.1016/S0040-4020(02)00674-9

Reference yield:

: 222986-35-8
(1R)-2-[(tert-butyldimethylsilyl)oxy]-1-(furan-2-yl)ethanol

: 475976-12-6
(2S,3S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / diphenylphosphorazide; DBU / toluene / 10 h

2: hydrogen / 10 percent Pd/C / ethyl acetate / 0.67 h / 750.06 Torr

3: 2.57 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

4: 92 percent / m-chloroperbenzoic acide / CH₂Cl₂ / 4 h / 20 °C

5: 94 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / tetrahydrofuran / 3 h / 0 °C

6: 89 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.67 h / -30 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1016/S0040-4020(02)00674-9

Reference yield:

: (S)-(2-azido-2-furan-2-yl-ethoxy)-tert-butyl-dimethyl-silane

: 475976-12-6
(2S,3S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: hydrogen / 10 percent Pd/C / ethyl acetate / 0.67 h / 750.06 Torr

2: 2.57 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

3: 92 percent / m-chloroperbenzoic acide / CH₂Cl₂ / 4 h / 20 °C

4: 94 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / tetrahydrofuran / 3 h / 0 °C

5: 89 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.67 h / -30 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(02)00674-9