(2R,3R,4S)-methyl 4-acetoxy-2-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)-5-(phenylthio)pentanoate

Base Information

Chemical Name:(2R,3R,4S)-methyl 4-acetoxy-2-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)-5-(phenylthio)pentanoate
CAS No.:1383254-12-3
Molecular Formula:C₂₇H₃₆N₂O₆S
Molecular Weight:516.659
Hs Code.:

Synonyms:(2R,3R,4S)-methyl 4-acetoxy-2-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)-5-(phenylthio)pentanoate

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Chemical Property of (2R,3R,4S)-methyl 4-acetoxy-2-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)-5-(phenylthio)pentanoate

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Technology Process of (2R,3R,4S)-methyl 4-acetoxy-2-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)-5-(phenylthio)pentanoate

There total 6 articles about (2R,3R,4S)-methyl 4-acetoxy-2-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)-5-(phenylthio)pentanoate 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: 77.0%

: 1383254-05-4
(2R)-methyl 2-[(4R,5S)-(5-acetyloxy-3-tert-butoxycarbonylamino-2,2-dioxide-1,2,3-oxathiazine-tetrahydro-4-yl)-2-benzyl(methyl)amino]acetate

: 108-98-5
thiophenol

: 1383254-12-3
(2R,3R,4S)-methyl 4-acetoxy-2-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)-5-(phenylthio)pentanoate

Guidance literature:: With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 1.5h;
DOI:10.1021/jo300468j

Reference yield:

: 1383254-04-3
(2R)-methyl 2-[(4R,5S)-(5-acetyloxy-2,2-dioxide-1,2,3-oxa-thiazine-tetrahydro-4-yl)-2-benzyl(methyl)amino]acetate

: 1383254-12-3
(2R,3R,4S)-methyl 4-acetoxy-2-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)-5-(phenylthio)pentanoate

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; triethylamine / N,N-dimethyl-formamide / 4 h

2: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 °C

With dmap; sodium hydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo300468j

Reference yield:

: 1383253-94-8
(4aS,7R,7aR)-7-[benzyl(methyl)amino]tetrahydrofuro[3,2-d]-[1,2,3]oxathiazin-6(1H)-one 2,2-dioxide

: 1383254-12-3
(2R,3R,4S)-methyl 4-acetoxy-2-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)-5-(phenylthio)pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1: methanol / 96 h / 20 °C

2: pyridine / 4 h / 20 °C

3: dmap; triethylamine / N,N-dimethyl-formamide / 4 h

4: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 °C

With pyridine; dmap; sodium hydride; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo300468j