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

Base Information

• Chemical Name: O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
• CAS No.: 100752-65-6
• Molecular Formula: C₄₇H₅₂N₆O₁₄
• Molecular Weight: 924.962
• Mol file: 100752-65-6.mol

Synonyms:O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Chemical Property of O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

There total 12 articles about O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 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:

O-(methyl 2,3-di-O-benzyl-4-O-(chloroacetyl)-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (87907-02-6) → O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (100752-65-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / thiourea / ethanol / 6 h / Heating

2: 69 percent Turnov_. / mercuric bromide, molecular sieves 4A / CH₂Cl₂ / 72 h / Ambient temperature

3: M sodium hydroxide / methanol; H₂O / 1.) 0-5 deg C 2.) r.t., 3 h

4: methanol; diethyl ether

With sodium hydroxide; 4 A molecular sieve; thiourea; mercury dibromide; In methanol; diethyl ether; ethanol; dichloromethane; water;

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-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (100752-65-6)

Guidance literature:

Multi-step reaction with 11 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

3: 94 percent / cupric chloride dihydrate / various solvent(s); ethanol / 1 h / Heating

4: pyridine / 4 h / 85 °C

5: pyridine / 1.) 0-5 deg C 2.) r.t., 30 min

6: Jones's reagent (4M chromium trioxide) / acetone / 1.) 0-5 deg C 2.) r.t., 50 min

7: CH₂Cl₂; diethyl ether

8: 71 percent / thiourea / ethanol / 6 h / Heating

9: 69 percent Turnov_. / mercuric bromide, molecular sieves 4A / CH₂Cl₂ / 72 h / Ambient temperature

10: M sodium hydroxide / methanol; H₂O / 1.) 0-5 deg C 2.) r.t., 3 h

11: methanol; diethyl ether

With pyridine; chromium(VI) oxide; sodium hydroxide; sodium azide; 4 A molecular sieve; ammonium chloride; thiourea; mercury dibromide; copper dichloride; In methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

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

Reference yield:

O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (99541-24-9) → O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (100752-65-6)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / 4 h / 85 °C

2: pyridine / 1.) 0-5 deg C 2.) r.t., 30 min

3: Jones's reagent (4M chromium trioxide) / acetone / 1.) 0-5 deg C 2.) r.t., 50 min

4: CH₂Cl₂; diethyl ether

5: 71 percent / thiourea / ethanol / 6 h / Heating

6: 69 percent Turnov_. / mercuric bromide, molecular sieves 4A / CH₂Cl₂ / 72 h / Ambient temperature

7: M sodium hydroxide / methanol; H₂O / 1.) 0-5 deg C 2.) r.t., 3 h

8: methanol; diethyl ether

With pyridine; chromium(VI) oxide; sodium hydroxide; 4 A molecular sieve; thiourea; mercury dibromide; In methanol; diethyl ether; ethanol; dichloromethane; water; acetone;

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

upstream raw materials:

diazomethane

(2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid

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

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

Refernces