[6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate

Base Information

• Chemical Name: [6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate
• CAS No.: 796873-41-1
• Molecular Formula: C₃₀H₃₅Cl₃N₄O₁₅
• Molecular Weight: 797.985
• Mol file: 796873-41-1.mol

Synonyms:[6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate

Chemical Property of [6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate

There total 8 articles about [6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-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: 81.0%

trichloroacetonitrile (545-06-2) + 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-D-glucopyranose → [6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate (796873-41-1)

Guidance literature:

With potassium carbonate; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.carres.2004.07.018

Reference yield:

methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside (104707-00-8) → [6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate (796873-41-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 74 percent / N-idosuccinimide; silver triflate / CH₂Cl₂

2: 100 percent / NaOMe / methanol; tetrahydrofuran / 48 h / 20 °C

3: KBr; 1,2,6,6-tetramethylpiperidine-1-oxide; NaOCl / aq. NaHCO₃; tetrahydrofuran / 0.5 h / 20 °C

4: dimethylformamide / 12 h

5: 1.68 percent / DMAP / dimethylformamide / 12 h / 20 °C

6: 100 percent / TFA / 12 h / 20 °C

7: 65 percent / benzylamine / diethyl ether / 1 h / 0 °C

8: 81 percent / K₂CO₃ / CH₂Cl₂ / 12 h / 20 °C

With dmap; sodium hypochlorite; N-iodo-succinimide; 1,2,6,6-tetramethylpiperidine-1-oxide; sodium methylate; silver trifluoromethanesulfonate; potassium carbonate; benzylamine; trifluoroacetic acid; potassium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; sodium hydrogencarbonate; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2004.07.018

Reference yield:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose (796873-39-7) → [6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate (796873-41-1)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethylformamide / 12 h

2: 1.68 percent / DMAP / dimethylformamide / 12 h / 20 °C

3: 100 percent / TFA / 12 h / 20 °C

4: 65 percent / benzylamine / diethyl ether / 1 h / 0 °C

5: 81 percent / K₂CO₃ / CH₂Cl₂ / 12 h / 20 °C

With dmap; potassium carbonate; benzylamine; trifluoroacetic acid; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2004.07.018

upstream raw materials:

trichloroacetonitrile

methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

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

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose

Downstream raw materials:

methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside