108811-27-4

Basic information

• Product Name: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranose
• Synonyms: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranose
• CAS NO: 108811-27-4
• Molecular Weight: 973.173
• Mol File: 108811-27-4.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranose(108811-27-4)
• EPA Substance Registry System: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranose(108811-27-4)

Safety Data

• Hazardous Substances Data: 108811-27-4(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 115969-50-1 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 84396-49-6 allyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1[*]4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 62746-92-3 benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 28022-14-2 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 5328-50-7 D-cellobiose octaacetate 
• 88567-59-3 phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 62746-91-2 C₆₈H₇₀O₁₁ 
• 27891-73-2 β-phenylsulfanyl lactoside 
• 5346-81-6 phenyl 2,3,6-tri-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 
• 3616-19-1 lactose octaacetate 
• 183064-37-1 phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 126777-84-2 2-methoxyethyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 5160-10-1 2,3,6-tetra-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucopyranosylbromide 

Downstream Products

• 83921-72-6 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 83921-71-5 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 144946-83-8 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-D-glucose oxime 
• 149300-00-5 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranosyl fluoride 
• 1562507-65-6 3,4,7-tri-O-benyl-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-D-glucphept-1-enitol 
• 1562507-92-9 dibenzyl 2,3,6,2',3',4',6'hepta-O-benzyl-α-D-maltosyl phosphate 
• 80312-32-9 4-O-α-D-glucopyranosyl-(1->4)-1-deoxynojirimycin 

Relevant articles and documents

Regioselective Anomeric O-Benzyl Deprotection in Carbohydrates

A highly regioselective hydrogenolysis of the anomeric benzyl group is reported. The reaction involves selective acetolysis of benzyl acetals of various mono- and di-saccharides using 10 % Pd/C under hydrogen atmosphere in the presence of Na2CO

Synthesis of Glycosylated 1-Deoxynojirimycins Starting from Natural and Synthetic Disaccharides

Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bioorganic chemistry and medicinal chemistry, yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1-deoxynojirimycin derivatives based on the oxidation–reductive amination protocol that in the past has also been shown to be a versatile route towards 1-deoxynojirimycin. The strategy can be applied on commercial disaccharides, as shown in four examples, as well as on disaccharides that are not commercially available and are synthesized for this purpose, as shown by a fifth example.

Synthesis of a C-phosphonate mimic of maltose-1-phosphate and inhibition studies on Mycobacterium tuberculosis GlgE

The emergence of extensively drug-resistant tuberculosis (XDR-TB) necessitates the need to identify new anti-tuberculosis drug targets as well as to better understand essential biosynthetic pathways. GlgE is a Mycobacterium tuberculosis (Mtb) encoded maltosyltransferase involved in α-glucan biosynthesis. Deletion of GlgE in Mtb results in the accumulation of M1P within cells leading to rapid death of the organism. To inhibit GlgE a maltose-C-phosphonate (MCP) 13 was designed to act as an isosteric non-hydrolysable mimic of M1P. MCP 13, the only known inhibitor of Mtb GlgE, was successfully synthesized using a Wittig olefination as a key step in transforming maltose to the desired product. MCP 13 inhibited Mtb GlgE with an IC50 = 230 ± 24 μM determined using a coupled enzyme assay which measures orthophosphate release. The requirement of M1P for the assay necessitated the development of an expedited synthetic route to M1P from an intermediate used in the MCP 13 synthesis. In conclusion, we designed a substrate analogue of M1P that is the first to exhibit Mtb GlgE inhibition.