2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-L-threose

Base Information

Chemical Name:2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-L-threose
CAS No.:145532-43-0
Molecular Formula:C₁₉H₂₇NO₅
Molecular Weight:349.427
Hs Code.:

Synonyms:2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-L-threose

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Chemical Property of 2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-L-threose

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Technology Process of 2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-L-threose

There total 13 articles about 2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-L-threose 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: 75.0%

: 437609-54-6
(4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 145532-43-0
2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-L-threose

Guidance literature:: With Chloro-oxo-acetic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/ol0200448

Reference yield:

: 100-39-0
benzyl bromide

: 145532-43-0
2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-L-threose

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / sodium hydride / dimethylformamide / 18 h / -5 - 20 °C

2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 0 - 20 °C

3: 75 percent / oxalylchloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With Chloro-oxo-acetic acid; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: Swern oxidation;
DOI:10.1021/ol0200448

Reference yield:

: 213338-89-7
(S)-3-(tert-butoxycarbonylamino)-2-methyleneoxetane

: 145532-43-0
2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-L-threose

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / dimethyldioxirane / CH₂Cl₂ / 1 h / -78 °C

2: 96 percent / CH₂Cl₂ / -78 - 20 °C

3: 88 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 96 h / 20 °C

4: 31 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

5: 94 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 0 - 20 °C

6: 95 percent / sodium hydride / dimethylformamide / 18 h / -5 - 20 °C

7: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 0 - 20 °C

8: 75 percent / oxalylchloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With dmap; Chloro-oxo-acetic acid; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 8: Swern oxidation;
DOI:10.1021/ol0200448