O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate
• CAS No.: 135362-96-8
• Molecular Formula: C₅₅H₆₀Cl₃N₇O₁₈
• Molecular Weight: 1213.48
• Mol file: 135362-96-8.mol

Synonyms:O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

Chemical Property of O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

There total 20 articles about O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate 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:

p-methylphenyl 2,3-di-O-benzyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside (850416-39-6) → O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate (135362-96-8) + O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate (135362-95-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: trifluoroacetic acid / dichloromethane; water / 0.33 h / 20 °C

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 5 h / 20 °C

3.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C

4.1: pyridine / dichloromethane / 6 h / 0 - 20 °C

5.1: iodine(I) bromide / dichloromethane / 4 h / 20 °C

6.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

6.2: 96 h / 20 °C / Molecular sieve; Inert atmosphere

7.1: thiourea / methanol; chloroform / 24 h / 60 °C

8.1: toluene / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

8.2: 2 h / -20 - 20 °C / Molecular sieve; Inert atmosphere

9.1: t-butyldimethylsiyl triflate / 0.33 h / 0 °C / Inert atmosphere; Cooling with ice

10.1: ammonia / methanol; tetrahydrofuran / 0 °C / Cooling with ice

11.1: potassium carbonate / dichloromethane / 20 °C / Inert atmosphere

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; t-butyldimethylsiyl triflate; ammonia; iodine(I) bromide; potassium carbonate; potassium hydrogencarbonate; thiourea; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/cmdc.201400019

Reference yield:

1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose (55682-48-9) → O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate (135362-96-8) + O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate (135362-95-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: t-butyldimethylsiyl triflate / 0.33 h / 0 °C

2.1: ammonia / methanol; tetrahydrofuran / 0 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C

4.1: toluene / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

4.2: 2 h / -20 - 20 °C / Molecular sieve; Inert atmosphere

5.1: t-butyldimethylsiyl triflate / 0.33 h / 0 °C / Inert atmosphere; Cooling with ice

6.1: ammonia / methanol; tetrahydrofuran / 0 °C / Cooling with ice

7.1: potassium carbonate / dichloromethane / 20 °C / Inert atmosphere

With t-butyldimethylsiyl triflate; ammonia; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1002/cmdc.201400019

Reference yield:

O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranose + trichloroacetonitrile (545-06-2) → O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate (135362-96-8) + O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate (135362-95-7)

Guidance literature:

With potassium carbonate; In dichloromethane; at 20 ℃; Overall yield = 81 %; Overall yield = 490 mg; Inert atmosphere;

DOI:10.1002/cmdc.201400019

upstream raw materials:

1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranose

O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

1,6-anhydro-2-azide-4-O-(tert-buthyldimethylsilyl)-2-deoxy-β-D-glucopyranose

3-O-acetyl-1,6-anhydro-2-azido-4-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

Refernces