phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside
• CAS No.: 370554-13-5
• Molecular Formula: C₂₆H₂₅N₃O₄S
• Molecular Weight: 475.568

Synonyms:phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

There total 5 articles about phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 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: 77.2%

benzyl bromide (100-39-0) + phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (819798-40-8) → phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (370554-13-5)

Guidance literature:

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

thiophenol (108-98-5) + (2S,4aR,7R,8R,8aR)-7-Azido-8-benzyloxy-6-chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (625388-51-4) → phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (370554-13-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1246/bcsj.76.1829

Reference yield:

sodium thiophenolate (930-69-8) + (2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (370554-12-4) → phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (370554-13-5)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1246/cl.2001.840

upstream raw materials:

sodium thiophenolate

(2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

thiophenol

(2S,4aR,7R,8R,8aR)-7-Azido-8-benzyloxy-6-chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Downstream raw materials:

O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine benzyl ester

phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-β-D-galactopyranoside

phenyl 4-O-(2-azido-3-O-benzoyl-4-phthalimido-2,4,6-trideoxy-α-D-galactopyranosyl)-2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-β-D-galactopyranoside

phenyl 4-O-(2-azido-4-benzyloxycarbonylamino-2,4,6-trideoxy-α-D-galactopyranosyl)-2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-β-D-galactopyranoside

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