5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: 5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside
• CAS No.: 270075-77-9
• Molecular Formula: C₄₈H₇₅N₃O₁₅
• Molecular Weight: 934.135
• Mol file: 270075-77-9.mol

Synonyms:5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Chemical Property of 5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

There total 20 articles about 5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside 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: 90.0%

5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside (270075-76-8) → 5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside (270075-77-9)

Guidance literature:

With pyridine; thiourea; In N,N-dimethyl-formamide; at 22 ℃; for 2h;

DOI:10.1016/j.carres.2006.04.006

Reference yield:

phenyl 2-azido-2-deoxy-4,6-O-diphenylmethylidene-1-thio-β-D-glucopyranoside (904690-67-1) → 5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside (270075-77-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / 2,4,6-tri-tert-butylpyrimidine / CH₂Cl₂ / 1 h / 0 °C

2: 89 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 1 h / 0 - 22 °C

3: trifluoroacetic acid; aq. HCl / 0.25 h / 22 °C

4: 6.4 g / 4-dimethylaminopyridine / pyridine / 0.33 h / 22 °C

5: 90 percent / thiourea; pyridine / dimethylformamide / 2 h / 22 °C

With pyridine; hydrogenchloride; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; thiourea; trifluoroacetic acid; 2,4,6-tri-tert-butylpyrimidine; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.04.006

Reference yield:

phenyl 2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-diphenylmethylidene-1-thio-β-D-glucopyranoside (904690-68-2) → 5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside (270075-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 1 h / 0 - 22 °C

2: trifluoroacetic acid; aq. HCl / 0.25 h / 22 °C

3: 6.4 g / 4-dimethylaminopyridine / pyridine / 0.33 h / 22 °C

4: 90 percent / thiourea; pyridine / dimethylformamide / 2 h / 22 °C

With pyridine; hydrogenchloride; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; thiourea; trifluoroacetic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.04.006

upstream raw materials:

5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

phenyl 2-azido-2-deoxy-4,6-O-diphenylmethylidene-1-thio-β-D-glucopyranoside

phenyl 2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-diphenylmethylidene-1-thio-β-D-glucopyranoside

5-(methoxycarbonyl)pentyl 2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-diphenylmethylidene-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside