2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate
• CAS No.: 1415663-28-3
• Molecular Formula: C₂₄H₂₇Cl₃N₂O₅
• Molecular Weight: 529.848
• Mol file: 1415663-28-3.mol

Synonyms:2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate

Chemical Property of 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate

There total 12 articles about 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-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: 79.0%

2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose + trichloroacetonitrile (545-06-2) → 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate (1415663-28-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1016/j.bmcl.2013.09.083

Reference yield:

methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside (1415663-21-6) → 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate (1415663-28-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid; sulfuric acid / 48 h / Inert atmosphere

2.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 8 h / 50 °C / Inert atmosphere

3.1: dichloromethane / 0.17 h / 0 °C / Inert atmosphere

3.2: 4 h / Inert atmosphere

With sulfuric acid; hydrazinium monoacetate; acetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield:

1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose (1415663-22-7) → 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate (1415663-28-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 8 h / 50 °C / Inert atmosphere

2.1: dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.2: 4 h / Inert atmosphere

With hydrazinium monoacetate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2012.10.064

upstream raw materials:

benzaldehyde dimethyl acetal

methyl 2,3-di-O-benzoyl-4-O-benzyl-α-D-glucopyranoside

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-deoxy-α-D-glucopyranoside

Downstream raw materials:

5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A?11,12-cyclic carbonate

5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate