2-O-Acetyl-3,4,6-tri-O-benzyl-a-D-mannopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2-O-Acetyl-3,4,6-tri-O-benzyl-a-D-mannopyranosyl trichloroacetimidate
• CAS No.: 108869-64-3
• Molecular Formula: C31H32Cl3NO7
• Molecular Weight: 636.957
• Mol file: 108869-64-3.mol

Synonyms:2-O-Acetyl-3,4,6-tri-O-benzyl-a-D-mannopyranosyl trichloroacetimidate;3,4,6-Tris-O-(phenylmethyl)-alpha-D-glucopyranose 2-acetate 1-(2,2,2-trichloroethanimidate)

Chemical Property of 2-O-Acetyl-3,4,6-tri-O-benzyl-a-D-mannopyranosyl trichloroacetimidate

Chemical Property:

• PSA: 96.30000
• LogP: 6.49440

Purity/Quality:

97% ^*data from raw suppliers

2-O-Acetyl-3,4,6-tri-O-benzyl-a-D-mannopyranosyl trichloroacetimidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-O-Acetyl-3,4,6-tri-O-benzyl-a-D-mannopyranosyl trichloroacetimidate

There total 37 articles about 2-O-Acetyl-3,4,6-tri-O-benzyl-a-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: 99.0%

2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose (79218-68-1,88988-46-9,93495-88-6,108869-76-7,127875-27-8,127875-34-7,129214-38-6,148968-88-1) + trichloroacetonitrile (545-06-2) → 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate (108869-64-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.carres.2010.01.015

Reference yield: 98.0%

2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside (129214-38-6) + trichloroacetonitrile (545-06-2) → 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (108869-64-3,130177-78-5,129163-12-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dichloro-ethane; for 0.166667h;

DOI:10.1016/0008-6215(90)84223-H

Reference yield: 93.0%

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside (79218-68-1) + trichloroacetonitrile (545-06-2) → 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (108869-64-3,130177-78-5,129163-12-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene;

upstream raw materials:

2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside

trichloroacetonitrile

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose

Downstream raw materials:

8-Methoxycarbonyloctyl-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid

Octyl-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid

Octyl-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-3-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosid

methyl 2,4-di-O-benzyl-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→3))-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→6))-α-D-mannopyranoside

Refernces

• 1、 Lubineau, Andre,Drouillat, Bruno. "Lithium triflate as a new promoter of glycosylation under neutral conditions". . p. 1179 - 1186. Retrieved 1997.
• 2、 Chesnokov, Gleb A.,Gademann, Karl. "Concise Total Synthesis of Peyssonnoside A". . p. 14083 - 14088. Retrieved 2021.
• 3、 Matovi?, Jelena,J?rvinen, Juulia,Sokka, Iris K.,Imlimthan, Surachet,Raitanen, Jan-Erik,Montaser, Ahmed,Maaheimo, Hannu,Huttunen, Kristiina M.,Per?niemi, Sirpa,Airaksinen, Anu J.,Sarparanta, Mirkka,Johansson, Mikael P.,Rautio, Jarkko,Ekholm, Filip S.. "Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates". . p. 285 - 304. Retrieved 2020/12/21.