308290-86-0

Basic information

• Product Name: 2'',5',6''-tri-O-benzyl-2',3'',4''-tris(dibenzyloxyphosphoryl)-3'-O-α-D-glucopyranosyl-1-β-D-ribofuranosidoimidazole
• Synonyms: 2'',5',6''-tri-O-benzyl-2',3'',4''-tris(dibenzyloxyphosphoryl)-3'-O-α-D-glucopyranosyl-1-β-D-ribofuranosidoimidazole
• CAS NO: 308290-86-0
• Molecular Weight: 1413.4
• Mol File: 308290-86-0.mol

Chemical Properties

• CAS DataBase Reference: 2'',5',6''-tri-O-benzyl-2',3'',4''-tris(dibenzyloxyphosphoryl)-3'-O-α-D-glucopyranosyl-1-β-D-ribofuranosidoimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2'',5',6''-tri-O-benzyl-2',3'',4''-tris(dibenzyloxyphosphoryl)-3'-O-α-D-glucopyranosyl-1-β-D-ribofuranosidoimidazole(308290-86-0)
• EPA Substance Registry System: 2'',5',6''-tri-O-benzyl-2',3'',4''-tris(dibenzyloxyphosphoryl)-3'-O-α-D-glucopyranosyl-1-β-D-ribofuranosidoimidazole(308290-86-0)

Safety Data

• Hazardous Substances Data: 308290-86-0(Hazardous Substances Data)

Upstream product

• 169822-03-1 allyl 2,6-di-O-benzyl-α-D-glucopyranoside 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 31504-85-5 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-xylofuranose 
• 2592-42-9 5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 34311-63-2 5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose 
• 23202-83-7 5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 308290-84-8 2',3'',4''-tri-O-acetyl-2'',5',6''-tri-O-benzyl-3'-O-α-D-glucopyranosyl-1-β-D-ribofuranosidoimidazole 
• 308290-85-9 2'',5',6''-tri-O-benzyl-3'-O-α-D-glucopyranosyl-1-β-D-ribofuranosidoimidazole 
• 197644-83-0 1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-α/β-D-ribofuranoside 
• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 264230-04-8 3,4-di-O-acetyl-2,6-di-O-benzyl-D-glucopyranosyl dimethyl phosphite 
• 178319-07-8 allyl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

Convergent synthesis of adenophostin A analogues via a base replacement strategy

The first totally synthetic base-modified analogues of the natural product and potent D-myo-inositol 1,4,5-trisphosphate receptor agonist adenophostin A were efficiently synthesised from D-xylose and D-glucose using methodology employing base and surrogate base addition to a common disaccharide intermediate.

Contribution of the adenine base to the activity of adenophostin A investigated using a base replacement strategy

Syntheses of 3'-O-α-D-glucopyranosyl-1-β-D-ribofuranosidoimidazole 2',3',4'-trisphosphate (7) and 3'-O-α-D-glucopyranosyl-9-β-D-ribofuranosidopurine 2',3',4'-trisphosphate (8), two analogues of the superpotent 1D-myo-inositol 1,4,5-trisphosphate receptor agonist adenophostin A (2), are described. 5-O-Benzyl-1,2-O-isopropylidene-α-D-ribofuranose was prepared by an improved route from 1,2-O-isopropylidene-α-D-xylofuranose and was coupled with 3,4-di-O-acetyl-2,6-di-O-benzyl-D-glucopyranosyl dimethyl phosphite to give 3',4'-di-O-acetyl-2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-1,2-O-isopropy lidene-α-D-ribofuranose. Removal of the isopropylidene acetal and subsequent acetylation gave the central disaccharide 1,2,3',4'-tetra-O-acetyl-2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-D-ribof uranose. Vorbruggen condensation with activated imidazole or purine gave the required β-substituted derivatives which were further elaborated to 7 and 8, respectively. Radioligand binding assays to hepatic InsP3 receptors and functional assays of Ca2+ release from permeabilized hepatocytes gave a rank order of potency of the ligands 2 ? 8 > 7 ? Ins(1,4,5)P3 indicating that the N6-amino group of 2 is of little importance for activity and that a minimum of a two-fused-ring nucleobase is required for activity to exceed that of Ins(1,4,5)P3. The role of the adenine base in the activity of the adenophostins is discussed. This general method should facilitate ready access to nucleobase-modified adenophostin analogues for SAR studies.