Acetic acid (2R,3S)-2-acetoxymethyl-1-benzoyl-1,2,3,6-tetrahydro-pyridin-3-yl ester

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Chemical Name:Acetic acid (2R,3S)-2-acetoxymethyl-1-benzoyl-1,2,3,6-tetrahydro-pyridin-3-yl ester
CAS No.:201946-60-3
Molecular Formula:C₁₇H₁₉NO₅
Molecular Weight:317.342
Hs Code.:

Synonyms:Acetic acid (2R,3S)-2-acetoxymethyl-1-benzoyl-1,2,3,6-tetrahydro-pyridin-3-yl ester

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Chemical Property of Acetic acid (2R,3S)-2-acetoxymethyl-1-benzoyl-1,2,3,6-tetrahydro-pyridin-3-yl ester

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Technology Process of Acetic acid (2R,3S)-2-acetoxymethyl-1-benzoyl-1,2,3,6-tetrahydro-pyridin-3-yl ester

There total 6 articles about Acetic acid (2R,3S)-2-acetoxymethyl-1-benzoyl-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: 46.0%

: Acetic acid (E)-(S)-1-[(R)-2-acetoxy-1-(benzoyl-trimethylsilanylmethyl-amino)-ethyl]-3-trimethylsilanyl-allyl ester

: 201946-60-3
Acetic acid (2R,3S)-2-acetoxymethyl-1-benzoyl-1,2,3,6-tetrahydro-pyridin-3-yl ester

Guidance literature:: With ammonium cerium(IV) nitrate; In acetonitrile; at 40 ℃; for 20h;
DOI:10.1021/jo971706n

Reference yield:

: 201946-53-4
N-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-N-trimethylsilanylmethyl-benzamide

: 201946-60-3
Acetic acid (2R,3S)-2-acetoxymethyl-1-benzoyl-1,2,3,6-tetrahydro-pyridin-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1h, then 25 deg C, 3 h, 2.) THF, hexane, -78 deg C, 2 h, then 25 deg C, 0.5 h

2: 87 percent / aq. HF / acetonitrile / 0.5 h / 25 °C

3: 93 percent / 4-DMAP / pyridine / 17 h / 25 °C

4: 46 percent / (NH₄)2Ce(NO₃)6 / acetonitrile / 20 h / 40 °C

With dmap; n-butyllithium; ammonium cerium(IV) nitrate; hydrogen fluoride; In pyridine; acetonitrile;
DOI:10.1021/jo971706n

Reference yield:

: 201946-52-3
N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-N-trimethylsilanylmethyl-benzamide

: 201946-60-3
Acetic acid (2R,3S)-2-acetoxymethyl-1-benzoyl-1,2,3,6-tetrahydro-pyridin-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, 25 deg C, 2.5 h

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1h, then 25 deg C, 3 h, 2.) THF, hexane, -78 deg C, 2 h, then 25 deg C, 0.5 h

3: 87 percent / aq. HF / acetonitrile / 0.5 h / 25 °C

4: 93 percent / 4-DMAP / pyridine / 17 h / 25 °C

5: 46 percent / (NH₄)2Ce(NO₃)6 / acetonitrile / 20 h / 40 °C

With dmap; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; hydrogen fluoride; dimethyl sulfoxide; triethylamine; In pyridine; acetonitrile;
DOI:10.1021/jo971706n