6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose

Base Information

• Chemical Name: 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose
• CAS No.: 146197-09-3
• Molecular Formula: C₂₇H₂₇ClF₂O₄
• Molecular Weight: 488.959
• Mol file: 146197-09-3.mol

Synonyms:

Chemical Property of 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose

There total 3 articles about 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-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:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose (146197-09-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -40 deg C, 1 h, 2.) CH₂Cl₂, a) -40 deg, 15 min, b) 20 deg C, 1 h

2: 60 percent / diethylaminosulfur trifluoride (DAST) / CH₂Cl₂ / 18 h / 20 °C

3: 48 percent / 3N HCl / acetic acid / 4.5 h / 90 - 100 °C

4: SOCl₂ / dimethylformamide; CH₂Cl₂ / 0.75 h / 20 °C

With hydrogenchloride; thionyl chloride; oxalyl dichloride; diethylamino-sulfur trifluoride; dimethyl sulfoxide; triethylamine; In dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0022-1139(00)82408-2

Reference yield:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) → 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose (146197-09-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / diethylaminosulfur trifluoride (DAST) / CH₂Cl₂ / 18 h / 20 °C

2: 48 percent / 3N HCl / acetic acid / 4.5 h / 90 - 100 °C

3: SOCl₂ / dimethylformamide; CH₂Cl₂ / 0.75 h / 20 °C

With hydrogenchloride; thionyl chloride; diethylamino-sulfur trifluoride; In dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0022-1139(00)82408-2

Reference yield:

methyl 2,3,4-tri-O-benzyl-6-deoxy-6,6-difluoro-α-D-glucopyranoside (146197-18-4) → 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose (146197-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / 3N HCl / acetic acid / 4.5 h / 90 - 100 °C

2: SOCl₂ / dimethylformamide; CH₂Cl₂ / 0.75 h / 20 °C

With hydrogenchloride; thionyl chloride; In dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0022-1139(00)82408-2

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-deoxy-6,6-difluoro-α-D-glucopyranoside