2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetate

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetate
• CAS No.: 178681-00-0
• Molecular Formula: C₃₆H₃₅Cl₃O₇
• Molecular Weight: 686.029
• Mol file: 178681-00-0.mol

Synonyms:2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetate

Chemical Property of 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetate

There total 2 articles about 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetate 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:

2,3,4,6-tetra-O-benzyl-D-mannopyranose (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5) + trifluoroacetyl chloride (76-02-8) → 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl trichloroacetate (1330629-63-4) + 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetate (178681-00-0)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 1.5h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tet.2011.06.006

Reference yield:

2,3,4,6-tetra-O-benzyl-D-mannopyranose (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5) + trichloroacetic acid anhydride (4124-31-6) → 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetate (178681-00-0)

Guidance literature:

With CCl₃O₂^(1-)*Na⁽¹⁺⁾; In dichloromethane; for 0.5h; Yield given; Heating;

DOI:10.1080/07328309608005669

Reference yield: 85.0%

benzoic acid (65-85-0,8013-63-6) + 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetate (178681-00-0) → Benzoic acid (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1.) -20 deg C, 4 h, 2.) -20 deg C to r.t.;

DOI:10.1080/07328309608005669

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-mannopyranose

trichloroacetic acid anhydride

trifluoroacetyl chloride

Downstream raw materials:

methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

4-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside

isopropyl-O-2,3,4,6-tetra-O-benzyl-β-D-mannopyranose

(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-isopropoxytetrahydro-2H-pyran

Refernces

• 1、 Li, Zhong-Jun,Huang, He-Qing,Cai, Meng-Shen. "Studies on glycosides XVI. The use of mannosyl trichloroacetate in the synthesis of α-mannosides and related oligosaccharides". . p. 501 - 506. Retrieved 2007/10/03.