(1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol

Base Information

Chemical Name:(1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol
CAS No.:115822-52-1
Molecular Formula:C₂₂H₃₀N₂O₅S
Molecular Weight:434.557
Hs Code.:

Synonyms:(1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol

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Chemical Property of (1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol

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Technology Process of (1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol

There total 6 articles about (1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol 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: 61.0%

: 79265-30-8
2-(trimethylsilyl)thiazole

: 115822-55-4
(4S,1'S)-4-(1'-benzyloxy-2'-oxoethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 115822-52-1
(1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol

: 104470-54-4
(1S,2R)-2,3-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 20h;
DOI:10.1021/jo00264a036

Reference yield: 11.0%

: 79265-30-8
2-(trimethylsilyl)thiazole

: 115822-55-4
(4S,1'S)-4-(1'-benzyloxy-2'-oxoethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 115822-52-1
(1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol

: 115889-53-7
(1R)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol

Guidance literature:: In tetrahydrofuran;
DOI:10.1021/jo00292a013

Reference yield:

: (S)-2,2-Dimethyl-4-(thiazol-2-yl-trimethylsilanyloxy-methyl)-oxazolidine-3-carboxylic acid tert-butyl ester

: 115822-52-1
(1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol

Guidance literature:: Multi-step reaction with 4 steps

1: tetra-n-butylammoniumfluoride / tetrahydrofuran / 1 h

2: 1) NaH 2) tetra-n-butylammonium iodide / 1) THF, 20 min, reflux 2) 12h

4: 63 percent / tetrahydrofuran

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;
DOI:10.1021/jo00292a013