benzoxazol-2-yl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:benzoxazol-2-yl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
CAS No.:1029121-53-6
Molecular Formula:C₄₁H₃₇NO₇S
Molecular Weight:687.813
Hs Code.:

Synonyms:benzoxazol-2-yl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

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Chemical Property of benzoxazol-2-yl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

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Technology Process of benzoxazol-2-yl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

There total 4 articles about benzoxazol-2-yl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 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: 83.0%

: 92689-41-3
3,4,6-tri-O-benzyl-1,2-O-[methoxy(phenyl)methylene]-β-D-glucopyranose

: 2382-96-9,118090-08-7
2-sulfanyl-1,3-benzoxazole

: 1029121-53-6
benzoxazol-2-yl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: With mercury dibromide; In acetonitrile; for 2.5h; Molecular sieve; Inert atmosphere; Reflux;
DOI:10.1021/ol800345j

Reference yield:

: 2382-96-9,118090-08-7
2-sulfanyl-1,3-benzoxazole

: Benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester

: 1029121-53-6
benzoxazol-2-yl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: 2-sulfanyl-1,3-benzoxazole; With potassium carbonate; In acetone; at 60 ℃; for 3h;

Benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester; With 18-crown-6 ether; In acetone; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1039/c7ob02966g

Reference yield:

: 98-88-4
benzoyl chloride

: 1029121-53-6
benzoxazol-2-yl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; triethylamine / dichloromethane / 18 h / 20 °C

2.1: bromine / dichloromethane / 1.08 h / 20 °C / Molecular sieve; Inert atmosphere

3.1: potassium carbonate / acetone / 3 h / 60 °C

3.2: 16 h / 20 °C / Inert atmosphere

With dmap; bromine; potassium carbonate; triethylamine; In dichloromethane; acetone;
DOI:10.1039/c7ob02966g