(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

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Chemical Name:(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
CAS No.:1314766-44-3
Molecular Formula:C₄₄H₆₆N₂O₁₃S
Molecular Weight:863.08
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 4 articles about (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 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: 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:

: 100-44-7
benzyl chloride

: 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:: Multi-step reaction with 2 steps

1.1: methanol; toluene-4-sulfonic acid / 3 h / 20 °C

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

2.2: 3 h / -15 °C / Inert atmosphere; Molecular sieve

With methanol; toluene-4-sulfonic acid; In dichloromethane;
DOI:10.1016/j.tet.2011.05.054

Reference yield:

: 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

: 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:: Multi-step reaction with 2 steps

1.1: methanol; toluene-4-sulfonic acid / 3 h / 20 °C

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

2.2: 3 h / -15 °C / Inert atmosphere; Molecular sieve

With methanol; toluene-4-sulfonic acid; In dichloromethane;
DOI:10.1016/j.tet.2011.05.054