90357-98-5

Basic information

• Product Name: dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate
• Synonyms: dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate
• CAS NO: 90357-98-5
• Molecular Weight: 800.885
• Mol File: 90357-98-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate(90357-98-5)
• EPA Substance Registry System: dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate(90357-98-5)

Safety Data

• Hazardous Substances Data: 90357-98-5(Hazardous Substances Data)

Upstream product

• 3866-62-4 2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose 
• 1623-08-1 phosphoric acid dibenzyl ester 
• 250691-64-6 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl iodide 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 990-91-0 dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 123417-05-0 dibenzyl phosphorofluoridate 

Downstream Products

• 991-43-5 guanosine 5'-diphospho-D-mannose 
• 14034-70-9 α-D-mannopyranosyl (bis(cyclohexylammonium)phosphate) 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 177696-56-9 1,5-anhydro-2,3,4,6-tetra-O-benzyl-α-D-manno-hexitol 
• 59-56-3 mannose-1-phosphate 

Relevant articles and documents

Chemical Synthesis of d -glycero- d -manno-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation

D-glycero-d-manno-Heptose 1,7-bisphosphate (HBP) is the precursor for heptose residues found in Gram-negative bacterial membrane surface glycoproteins and glycolipids. HBP β-anomer was recently reported to be a pathogen-associated molecular pattern (PAMP) that regulates TIFA-dependent immunity. Herein, we report the chemical synthesis of HBP α- and β-anomers, which highlights a C-7 carbon homologation via the Corey-Chaykovsky reaction, and the introduction of a phosphate group at the anomeric position using the Mitsunobu reaction. Furthermore, NF-κB reporter assaying revealed that HBP β-anomer activates the NF-κB signaling pathway.

Chemo-enzymic Synthesis of Guanosine 5'-Diphosphomannose (GDP-Mannose) and Selected Analogues

Guanosine 5'-diphosphomannose (GDP-mannose, 1) has been prepared via two routes from α-D-mannose 1-phosphate 5.The non-enzymic route involves coupling of the phosphate 5 to guanosine 5'-monophosphate dibutyl phosphinothioic anhydride (GMP-anhydride 11) to give compound 1 in 40percent yield.The enzymic routes require coupling of compound 5 with guanosine 5'-triphosphate (GTP) catalysed by GDP-mannose pyrophosphorylase (37percent).

Glycosyl Imidates, 10. - Glycosyl Phosphates from Glycosyl Trichloroacetimidates

The glycosyl trichloroacetimidates 1-α,β, 8-α, 11-α, 13-α, 15-α, and 17-α directly transfer the glycosyl moiety to phosphoric acid mono- and diesters.The acidity of the phosphoric acid derivatives used was sufficient for the activation of the trichloroacetimidates, therefore an additional acidic catalyst was not required.From the β-imidate 1-β α-glycosyl phosphate and from the α-imidates preferentially β-glycosyl phosphates were obtained.Reaction of dibenzyl phosphate (2a) and cetyl phosphate (2c) with 1-α demonstrated that β/α-anomerization iscatalyzed by traces of acid.The glycosyl phosphates 3a-α, 3a-β - 3c-β, 3f-α, 9a-β, and 9c-β were partly or totally deprotected.The structures of the synthezised compounds were assigned by 1H NMR spectroscopy and by comparison with literature data.