phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside

Base Information

Chemical Name:phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside
CAS No.:1207750-80-8
Molecular Formula:C₂₈H₂₈ClN₃O₅S
Molecular Weight:554.066
Hs Code.:

Synonyms:phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside

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Chemical Property of phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside

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Technology Process of phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside

There total 1 articles about phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,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: 74.0%

: 372494-01-4
((2R,3S,4R,5R)-5-Azido-3,4-bis-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-methanol

: 541-88-8
Chloroacetic anhydride

: 1207750-80-8
phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside

Guidance literature:: With pyridine; In dichloromethane; at -20 ℃;
DOI:10.1016/j.tet.2010.07.055

Reference yield: 90.0%

: 1207750-80-8
phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside

: 1207750-78-4
tert-butyl [2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-N-(4-nitro)benzenesulfonyl-L-iditol]uronate

: 1207750-82-0
(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-chloroacetyl-α-D-glucopyranosyl)-(1->4)-[tert-butyl [2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-N-(4-nitro)benzenesulfonyl-L-iditol]uronate]

Guidance literature:: phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside; tert-butyl [2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-N-(4-nitro)benzenesulfonyl-L-iditol]uronate; In diethyl ether; dichloromethane; at -30 ℃; for 1h; Molecular sieve; Inert atmosphere;

With Me₂S₂-Tf₂O; In diethyl ether; dichloromethane; for 0.0833333h; stereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.tetlet.2009.11.042

Reference yield: 86.0%

: 1207750-80-8
phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside

: 1207750-74-0
2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-6-O-(1-naphthyl)methyl-N-(4-nitro)benzenesulfonyl-L-iditol

: 1207750-81-9
(2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-6-O-(1-naphthyl)methyl-N-(4-nitro)benzenesulfonyl-L-iditol]

Guidance literature:: phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside; 2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-6-O-(1-naphthyl)methyl-N-(4-nitro)benzenesulfonyl-L-iditol; In diethyl ether; dichloromethane; at -30 ℃; for 1h; Molecular sieve; Inert atmosphere;

With Me₂S₂-Tf₂O; In diethyl ether; dichloromethane; for 0.0833333h; stereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.tetlet.2009.11.042