Phenyl 2-O,3-O-dibenzyl-4-azido-4,6-dideoxy-1-thio-beta-D-glucopyranoside

Base Information

Chemical Name:Phenyl 2-O,3-O-dibenzyl-4-azido-4,6-dideoxy-1-thio-beta-D-glucopyranoside
CAS No.:369631-91-4
Molecular Formula:C₂₆H₂₇N₃O₃S
Molecular Weight:461.585
Hs Code.:
DSSTox Substance ID:DTXSID601138282
Nikkaji Number:J1.625.184D

Synonyms:DTXSID601138282;369631-91-4;Phenyl 2-O,3-O-dibenzyl-4-azido-4,6-dideoxy-1-thio-beta-D-glucopyranoside;Phenyl 4-azido-4,6-dideoxy-2,3-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside

Suppliers and Price of Phenyl 2-O,3-O-dibenzyl-4-azido-4,6-dideoxy-1-thio-beta-D-glucopyranoside

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 1 raw suppliers

Chemical Property of Phenyl 2-O,3-O-dibenzyl-4-azido-4,6-dideoxy-1-thio-beta-D-glucopyranoside

Chemical Property:

XLogP3:6.4
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:9
Exact Mass:461.17731291
Heavy Atom Count:33
Complexity:614

Purity/Quality:: 95% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1C(C(C(C(O1)SC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)N=[N+]=[N-]
Isomeric SMILES:C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)SC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)N=[N+]=[N-]

Technology Process of Phenyl 2-O,3-O-dibenzyl-4-azido-4,6-dideoxy-1-thio-beta-D-glucopyranoside

There total 3 articles about Phenyl 2-O,3-O-dibenzyl-4-azido-4,6-dideoxy-1-thio-beta-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: 77.0%

: 124-63-0
methanesulfonyl chloride

: 369631-90-3
phenyl 2,3-di-O-benzyl-6-deoxy-1-thio-β-D-galactopyranoside

: 369631-91-4
phenyl 4-C-azido-2,3-di-O-benzyl-4,6-dideoxy-1-thio-β-D-glucopyranoside

Guidance literature:: methanesulfonyl chloride; phenyl 2,3-di-O-benzyl-6-deoxy-1-thio-β-D-galactopyranoside; In pyridine; at 0 ℃; for 2h;

With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 7h;
DOI:10.1081/SCC-100104831

Reference yield:

: 231623-55-5
phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside

: 369631-91-4
phenyl 4-C-azido-2,3-di-O-benzyl-4,6-dideoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 85 percent / pyridine / 20 °C

2.1: 87 percent / lithium triethylborohydride / tetrahydrofuran / 3 h

3.1: pyridine / 2 h / 0 °C

3.2: 77 percent / sodium azide / dimethylformamide / 7 h / 100 °C

With lithium triethylborohydride; In tetrahydrofuran; pyridine;
DOI:10.1081/SCC-100104831

Reference yield:

: 369631-95-8
Toluene-4-sulfonic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

: 369631-91-4
phenyl 4-C-azido-2,3-di-O-benzyl-4,6-dideoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 87 percent / lithium triethylborohydride / tetrahydrofuran / 3 h

2.1: pyridine / 2 h / 0 °C

2.2: 77 percent / sodium azide / dimethylformamide / 7 h / 100 °C

With lithium triethylborohydride; In tetrahydrofuran; pyridine;
DOI:10.1081/SCC-100104831