3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl trichloroacetimidate
• CAS No.: 1451181-04-6
• Molecular Formula: C₃₆H₃₂Cl₃F₂NO₇
• Molecular Weight: 735.008
• Mol file: 1451181-04-6.mol

Synonyms:3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl trichloroacetimidate

Chemical Property of 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl trichloroacetimidate

There total 1 articles about 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl 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: 96.0%

3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-D-mannopyranoside + trichloroacetonitrile (545-06-2) → 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl trichloroacetimidate (1451181-04-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ja405990z

Reference yield: 82.0%

3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl trichloroacetimidate (1451181-04-6) + C80H80F2O16S → branched pentamannoside

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 - 0 ℃; Molecular sieve;

Reference yield: 75.0%

ethyl 4-O-benzyl-2-O-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside (1451181-03-5) + 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl trichloroacetimidate (1451181-04-6) → ethyl 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)-[3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→6)]-4-O-benzyl-2-O-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside (1451181-05-7)

Guidance literature:

ethyl 4-O-benzyl-2-O-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside; 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl trichloroacetimidate; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere; Molecular sieve;

DOI:10.1021/ja405990z

upstream raw materials:

trichloroacetonitrile

Downstream raw materials:

ethyl 3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→3)-[3,4,6-tri-O-benzyl-2-O-(2,5-difluorobenzoyl)-α-D-mannopyranosyl-(1→6)]-4-O-benzyl-2-O-(2,5-difluorobenzoyl)-1-thio-α-D-mannopyranoside