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

Base Information

• Chemical Name: (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose
• CAS No.: 1379585-66-6
• Molecular Formula: C₃₄H₃₇N₃O₁₀
• Molecular Weight: 647.682
• Mol file: 1379585-66-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-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:

C33H35N3O10 + methyl iodide (74-88-4) → (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (1379585-66-6)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.3390/molecules21111602

Reference yield:

C33H35N3O10 + diazomethyl-trimethyl-silane (18107-18-1) → (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (1379585-66-6)

Guidance literature:

In methanol; diethyl ether; toluene; Inert atmosphere;

DOI:10.1016/j.carres.2012.03.014

Reference yield:

β-D-glucopyranosyl-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (796873-51-3) → (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (1379585-66-6)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid / tetrahydrofuran / Inert atmosphere

2: potassium iodide; silver(l) oxide / N,N-dimethyl-formamide / 6 h / 0 °C / Inert atmosphere; Darkness

3: methanol; camphor-10-sulfonic acid / dichloromethane / 48 h / Inert atmosphere

4: sodium hypochlorite; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; sodium hydrogencarbonate; sodium chloride; potassium bromide / water; ethyl acetate / 1 h / 0 °C

5: methanol; diethyl ether; toluene / Inert atmosphere

With methanol; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; camphor-10-sulfonic acid; tetrabutylammomium bromide; sodium hydrogencarbonate; toluene-4-sulfonic acid; potassium iodide; sodium chloride; potassium bromide; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.carres.2012.03.014

upstream raw materials:

diazomethyl-trimethyl-silane

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

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

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

Downstream raw materials:

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

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

Refernces

• 1、 Takeda, Naoko,Ikeda-Matsumi, Remina,Ebara-Nagahara, Kaoru,Otaki-Nanjo, Miyuki,Taniguchi-Morita, Kayo,Nanjo, Miwa,Tamura, Jun-Ichi. "Synthesis of heparan sulfate tetrasaccharide as a substrate for human heparanase". experimental part. p. 13 - 21. Retrieved 2012/07/02.