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

Base Information

Chemical Name:(2S,3S,6R)-benzoic acid 2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-yl ester
CAS No.:479411-03-5
Molecular Formula:C₂₇H₃₇NO₆SSi
Molecular Weight:531.745
Hs Code.:

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

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

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

There total 8 articles about (2S,3S,6R)-benzoic acid 2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-yl ester 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: 87.0%

: 98-88-4
benzoyl chloride

: 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

: 479411-03-5
(2S,3S,6R)-benzoic acid 2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-yl ester

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(02)00674-9

Reference yield:

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

: 479411-03-5
(2S,3S,6R)-benzoic acid 2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-yl ester

Guidance literature:: Multi-step reaction with 7 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

7: 87 percent / triethylamine / CH₂Cl₂ / 1 h / 20 °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

: 479411-03-5
(2S,3S,6R)-benzoic acid 2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-yl ester

Guidance literature:: Multi-step reaction with 6 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

6: 87 percent / triethylamine / CH₂Cl₂ / 1 h / 20 °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