.alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate)

Base Information

• Chemical Name: .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate)
• CAS No.: 183901-63-5
• Molecular Formula: C36H28 Cl3 N O10
• Molecular Weight: 740.978
• DSSTox Substance ID: DTXSID20449912
• Nikkaji Number: J941.937C
• Mol file: 183901-63-5.mol

Synonyms:.alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate)

Chemical Property of .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate)

Chemical Property:

• PSA: 147.51000
• LogP: 6.70890
• XLogP3: 9.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 15
• Exact Mass: 739.077879
• Heavy Atom Count: 50
• Complexity: 1170

Purity/Quality:

98% ^*data from raw suppliers

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl Trichloroacetimidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(C(O2)OC(=N)C(Cl)(Cl)Cl)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H]([C@@H]([C@H](O2)OC(=N)C(Cl)(Cl)Cl)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
• Uses: 2,3,4,6-Tetra-O-benzoyl-α-D-Mannopyranosyl TrichloroacetiMidate can be used for the preparation of mannosyl based dendrons for use as inhibitors treating microbial infections.

Technology Process of .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate)

There total 11 articles about .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate) 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: 98.0%

trichloroacetonitrile (545-06-2) + 2,3,4,6-tetra-O-benzoyl-α,β-D-mannospyranose (627466-98-2) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (183901-63-5)

Guidance literature:

base; for 12h;

DOI:10.1021/jo000432s

Reference yield: 94.0%

2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside (64768-20-3,66530-18-5,113544-55-1,121530-16-3,121530-28-7,135216-27-2,101857-05-0) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (183901-63-5)

Guidance literature:

With potassium carbonate; In dichloromethane;

DOI:10.1039/b712926b

Reference yield: 84.0%

alpha-D-mannopyranoside (7296-15-3) + benzoyl chloride (98-88-4) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (183901-63-5)

Guidance literature:

alpha-D-mannopyranoside; benzoyl chloride; With pyridine; In toluene; Reflux;

trichloroacetonitrile; With potassium carbonate; In dichloromethane; at 20 ℃; Inert atmosphere;

upstream raw materials:

trichloroacetonitrile

2,3,4,6-tetra-O-benzoyl-α,β-D-mannospyranose

2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside

1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside

Downstream raw materials:

C₅₅H₆₀O₁₂

8-(methoxycarbonyl)octyl (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->3)-[(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->6)]-α-D-mannopyranoside

2-[2-(2-chloroethoxy)ethoxy]ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside

5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside