(2S,3S)-benzoic acid 2-hydroxymethyl-6-oxo-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

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Chemical Name:(2S,3S)-benzoic acid 2-hydroxymethyl-6-oxo-1-(toluene-4-sulfonyl)-piperidin-3-yl ester
CAS No.:479411-06-8
Molecular Formula:C₂₀H₂₁NO₆S
Molecular Weight:403.456
Hs Code.:

Synonyms:(2S,3S)-benzoic acid 2-hydroxymethyl-6-oxo-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

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Chemical Property of (2S,3S)-benzoic acid 2-hydroxymethyl-6-oxo-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

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Technology Process of (2S,3S)-benzoic acid 2-hydroxymethyl-6-oxo-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

There total 12 articles about (2S,3S)-benzoic acid 2-hydroxymethyl-6-oxo-1-(toluene-4-sulfonyl)-piperidin-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: 93.0%

: 479411-05-7
(2S,3S)-benzoic acid 2-(tert-butyl-dimethyl-siloxymethyl)-6-oxo-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

: 479411-06-8
(2S,3S)-benzoic acid 2-hydroxymethyl-6-oxo-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h;
DOI:10.1016/S0040-4020(02)00674-9

Reference yield:

: 98-88-4
benzoyl chloride

: 479411-06-8
(2S,3S)-benzoic acid 2-hydroxymethyl-6-oxo-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

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

2: 92 percent / 4 Angstroem molecular sieves; m-chloroperbenzoic acid; BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

3: 89 percent / hydrogen / 10 percent Pd/C / methanol / 2 h / 750.06 Torr

4: 93 percent / TBAF / tetrahydrofuran / 2 h

With 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4020(02)00674-9

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 479411-06-8
(2S,3S)-benzoic acid 2-hydroxymethyl-6-oxo-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 2.57 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 92 percent / m-chloroperbenzoic acide / CH₂Cl₂ / 4 h / 20 °C

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

4: 89 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.67 h / -30 °C

5: 87 percent / triethylamine / CH₂Cl₂ / 1 h / 20 °C

6: 92 percent / 4 Angstroem molecular sieves; m-chloroperbenzoic acid; BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

7: 89 percent / hydrogen / 10 percent Pd/C / methanol / 2 h / 750.06 Torr

8: 93 percent / TBAF / tetrahydrofuran / 2 h

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