3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2R)-1-(benzyloxy)-2-(methanesulfonyl)propane

Base Information

Chemical Name:3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2R)-1-(benzyloxy)-2-(methanesulfonyl)propane
CAS No.:651031-29-7
Molecular Formula:C₂₆H₃₇NO₈S
Molecular Weight:523.648
Hs Code.:

Synonyms:3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2R)-1-(benzyloxy)-2-(methanesulfonyl)propane

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Chemical Property of 3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2R)-1-(benzyloxy)-2-(methanesulfonyl)propane

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Technology Process of 3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2R)-1-(benzyloxy)-2-(methanesulfonyl)propane

There total 11 articles about 3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2R)-1-(benzyloxy)-2-(methanesulfonyl)propane 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%

: 124-63-0
methanesulfonyl chloride

: 651031-28-6
3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2R)-1-(benzyloxy)propan-2-ol

: 651031-29-7
3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2R)-1-(benzyloxy)-2-(methanesulfonyl)propane

Guidance literature:: With dmap; triethylamine; In dichloromethane; at -30 ℃;
DOI:10.1021/ol035998s

Reference yield:

: 17325-85-8
(2S)-3-(benzyloxy)propane-1,2-diol

: 651031-29-7
3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2R)-1-(benzyloxy)-2-(methanesulfonyl)propane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

2.1: 77 percent / CH₂Cl₂ / -78 - 20 °C

3.1: NaH / tetrahydrofuran / 0.25 h / cooling

3.2: 81 percent / tetrahydrofuran / 2.17 h

4.1: 87 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / cooling

5.1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / -30 °C

With 2,6-dimethylpyridine; dmap; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol035998s

Reference yield:

: 79069-15-1
N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol

: 651031-29-7
3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2R)-1-(benzyloxy)-2-(methanesulfonyl)propane

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.25 h / cooling

1.2: 81 percent / tetrahydrofuran / 2.17 h

2.1: 87 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / cooling

3.1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / -30 °C

With dmap; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol035998s