b-D-Glucopyranose, 1,6-anhydro-2-azido-4-O-[2,3-bis-O-(phenylMethyl)-4,6-O-(phenylMethyl ene)-b-D-glucopyranosyl]-2-deoxy-, 3-acetate

Base Information

• Chemical Name: b-D-Glucopyranose, 1,6-anhydro-2-azido-4-O-[2,3-bis-O-(phenylMethyl)-4,6-O-(phenylMethyl ene)-b-D-glucopyranosyl]-2-deoxy-, 3-acetate
• CAS No.: 99541-23-8
• Molecular Formula: C35H37N3O10
• Molecular Weight: 659.693
• Mol file: 99541-23-8.mol

Synonyms:6,8-Dioxabicyclo[3.2.1]octane, β-D-glucopyranose deriv.;Pyrano[3,2-d]-1,3-dioxin, β-D-glucopyranose deriv.;

Chemical Property of b-D-Glucopyranose, 1,6-anhydro-2-azido-4-O-[2,3-bis-O-(phenylMethyl)-4,6-O-(phenylMethyl ene)-b-D-glucopyranosyl]-2-deoxy-, 3-acetate

Chemical Property:

• PSA: 149.89000
• LogP: 4.19996

Purity/Quality:

95% ^*data from raw suppliers

3-O-Acetyl-1,6-anhydro-2-azido-2',3'-di-O-benzyl-4',6'-O-benzylidene-2-deoxy-b-D-cellobiose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of b-D-Glucopyranose, 1,6-anhydro-2-azido-4-O-[2,3-bis-O-(phenylMethyl)-4,6-O-(phenylMethyl ene)-b-D-glucopyranosyl]-2-deoxy-, 3-acetate

There total 3 articles about b-D-Glucopyranose, 1,6-anhydro-2-azido-4-O-[2,3-bis-O-(phenylMethyl)-4,6-O-(phenylMethyl ene)-b-D-glucopyranosyl]-2-deoxy-, 3-acetate 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:

acetic anhydride (108-24-7) + (1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol (135415-93-9) → O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (99541-23-8)

Guidance literature:

With pyridine; In dichloromethane; Yield given; 1.) 0-5 deg C 2.) r.t., 3 h;

DOI:10.1016/S0008-6215(00)90458-0

Reference yield:

O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose (99541-22-7) → O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (99541-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide, ammonium chloride / dimethylformamide; H₂O / 37 h / 100 °C

2: pyridine / CH₂Cl₂ / 1.) 0-5 deg C 2.) r.t., 3 h

With pyridine; sodium azide; ammonium chloride; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90458-0

Reference yield:

2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose (99571-46-7) → O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (99541-23-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent Turnov_. / 1-tosylimidazole, sodium methoxide / CHCl₃; hexane / 5.5 h / Heating

2: sodium azide, ammonium chloride / dimethylformamide; H₂O / 37 h / 100 °C

3: pyridine / CH₂Cl₂ / 1.) 0-5 deg C 2.) r.t., 3 h

With pyridine; sodium azide; ammonium chloride; sodium methylate; N-tosylimidazole; In hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90458-0

upstream raw materials:

acetic anhydride

(1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose

2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose

Downstream raw materials:

O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-β-D-glucopyranose

6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-3,6-di-O-acetyl-β-D-glucopyranose

6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose