191097-63-9

Basic information

• Product Name: 3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)imidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranose
• Synonyms: 3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)imidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranose
• CAS NO: 191097-63-9
• Molecular Weight: 740.896
• Mol File: 191097-63-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)imidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)imidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranose(191097-63-9)
• EPA Substance Registry System: 3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)imidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranose(191097-63-9)

Safety Data

• Hazardous Substances Data: 191097-63-9(Hazardous Substances Data)

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 117740-07-5 1-benzyloxymethyl-2-methylimidazole 
• 615-15-6 2-Methyl-1H-benzimidazole 

Downstream Products

• 191097-84-4 acetyl-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)imidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranoside 
• 191097-85-5 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)imidazolyl]-1-deoxy-D-gluco-hept-2-enitol 

Relevant articles and documents

Synthesis and reactions of c-hetaryl substituted ketoses

O-Benzyl protected gluconolactone 1 reacts readily with 2-lithio derivatives of quinaldine, 2-methylquinoxaline, 2-methylbenzimidazole and N-protected derivatives, and 1-benzyloxymethyl-2-methylimidazole at low temperatures to afford as monoaddition products the corresponding D-gluco-2-heptuloses 2-5. The benzyl protective groups can be readily removed by hydrogenolysis as shown for the transformation of 4a into 8. Acylation reactions with 4a exhibited an interesting interplay between O-and N-acylation which is dependent on the nature of the acylating agent and on the reaction conditions. Reductive removal of the anomeric hydroxy group in 4a-c and 5 was readily performed via elimination products 18a-c and 23; their hydrogenation with Pd/C gave directly the O,N-deprotected C-β-D-glucopyranosylmethyl derivatives 21 and 25, respectively.