(2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol

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Chemical Name:(2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol
CAS No.:1314766-43-2
Molecular Formula:C₁₈H₂₄N₂O₄S
Molecular Weight:364.466
Hs Code.:

Synonyms:(2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol

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Chemical Property of (2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol

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Technology Process of (2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol

There total 1 articles about (2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol 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: 90.0%

: 115822-48-5
(S,S)-2-<(tert-butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1(1,3-thiazol-2-yl)propan-1-ol

: 100-44-7
benzyl chloride

: 1314766-43-2
(2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol

Guidance literature:: With methanol; toluene-4-sulfonic acid; at 20 ℃; for 3h;
DOI:10.1016/j.tet.2011.05.054

Reference yield: 82.0%

: 1314766-43-2
(2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol

: 118605-55-3
(2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranoside)-1-trichloroacetimidate

: 1314766-44-3
(2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-3-(thiazol-2-yl)-1,3-propanediol

Guidance literature:: (2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol; (2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranoside)-1-trichloroacetimidate; In dichloromethane; for 1h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -15 ℃; for 3h; stereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.tet.2011.05.054

Reference yield:

: 1314766-43-2
(2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol

: 1314766-48-7
(2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-icosanediol

Guidance literature:: Multi-step reaction with 7 steps

1.1: dichloromethane / 1 h / Molecular sieve; Inert atmosphere

1.2: 3 h / -15 °C / Inert atmosphere; Molecular sieve

2.1: trifluoroacetic acid / dichloromethane / 3 h

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

4.1: acetonitrile / 12 h / Reflux

5.1: sodium tetrahydroborate / methanol / 0.58 h / 0 - 20 °C

5.2: 1 h / 20 °C

6.1: methanol / 2 h / 20 °C

7.1: sodium cyanoborohydride / methanol / 2 h / 20 °C

With sodium tetrahydroborate; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2011.05.054