34339-69-0

Basic information

• Product Name: 3-O-(Phenylmethyl)-alpha-D-glucopyranosyl bromide triacetate
• Synonyms: 2,4,6-Tri-O-acetyl-3-O-benzyl-alpha-D-glucopyranosyl bromide;3-O-(Phenylmethyl)-alpha-D-glucopyranosyl bromide triacetate
• CAS NO: 34339-69-0
• Molecular Weight: 459.291
• Mol File: 34339-69-0.mol

Chemical Properties

• CAS DataBase Reference: 3-O-(Phenylmethyl)-alpha-D-glucopyranosyl bromide triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-(Phenylmethyl)-alpha-D-glucopyranosyl bromide triacetate(34339-69-0)
• EPA Substance Registry System: 3-O-(Phenylmethyl)-alpha-D-glucopyranosyl bromide triacetate(34339-69-0)

Safety Data

• Hazardous Substances Data: 34339-69-0(Hazardous Substances Data)

Upstream product

• 142130-43-6 2,4,6-tri-O-acetyl-3-O-benzyl-D-glucopyranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 

Downstream Products

• 110082-85-4 2,4,6-tri-O-acetyl-3-O-benzyl-β-(3',4'-dimethoxyphenyl)ethyl-β-D-glucopyranoside 
• 143419-05-0 N-[(2R,3R,4R,5S,6R)-4-((2S,3R,4S,5S,6S)-5-Azido-4-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethoxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide 
• 143419-04-9 N-[(2R,3R,4R,5S,6R)-4-((2S,3R,4S,5S,6S)-5-Azido-4-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide 
• 143419-13-0 Acetic acid (2R,3R,4R,5R,6R)-2-allyloxy-4-benzyloxy-6-benzyloxymethyl-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester 
• 143419-12-9 Acetic acid (2R,3R,4R,5R,6R)-2-allyloxy-4-benzyloxy-6-benzyloxymethyl-5-methanesulfonyloxy-tetrahydro-pyran-3-yl ester 
• 143419-01-6 Acetic acid (2R,3R,4S,5S,6S)-2-allyloxy-5-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 143419-02-7 Acetic acid (2R,3R,4S,5S,6S)-5-azido-4-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester 
• 143419-00-5 allyl 2-O-acetyl-3,6-di-O-benzyl-β-D-glucopyranoside 
• 143418-99-9 Acetic acid (2R,4aR,6R,7R,8S,8aR)-6-allyloxy-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 143419-08-3 allyl 2-O-acetyl-3-O-benzyl-β-D-glucopyranoside 
• 91738-41-9 5-<<2-O-(2,3,5-O-Acetyl-β-D-apiofuranosyl)-3-O-benzyl-4,6-O-benzyliden-β-D-glucopyranosyl>oxy>-2-hydroxybenzoesaeure-methylester 
• 91738-42-0 5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester 
• 91738-33-9 5-<(3-O-Benzyl-4,6-O-benzyliden-β-D-glucopyranosyl)oxy>-2-benzyloxybenzoesaeure-methylester 
• 91738-32-8 5-<(3-O-Benzyl-β-D-glucopyranosyl)oxy>-2-benzyloxybenzoesaeure-methylester 

Relevant articles and documents

Photocatalytic synthesis of glycosyl bromides

Sugar hemiacetals were smoothly transformed into the corresponding glycosyl bromides by treatment with carbon tetrabromide in N,N-dimethylformamide with tris(2,2′-bipyridyl)ruthenium(II) chloride as a catalyst under visible-light irradiation. Protecting groups commonly used in carbohydrate derivatives are unaffected by the mild conditions for bromination. Georg Thieme Verlag KG Stuttgart · New York.

Synthesis of glycyrrhetic acid diglycosides and their cytoprotective activities against CCl4-induced hepatic injury in vitro

Glycyrrhetic acid diglycosides 16, 24, 25, 42 and 46, with respectively β-D-glucuronopyranosyl-(1→3)-β-D-glucopyranose, -(1→6)-α-D-glucopyranose, -(1→6)-β-D-glucopyranose, -(1→6)-β-D-galactopyranose, and β-D-galacturonopyranosyl-(→2)-β-D-glucopyranose as sugar components at the O-3 positions on the aglycons, were synthesized. In vitro cytoprotective activities, against CCl4-induced hepatic injury, of the synthetic diglycosides, methyl β-D-glucuronopyranosyl-(1→4)-α-D-glucopyranosyl-D-glycyrrhe tinate 33 and methyl esters 15 and 23 (the precursors of 16 and 24 respectively) were compared with those of glycyrrhizin 1 and β-D-glucuronopyranosyl-(1→2)-β-D-glucopyranosyl-glycyrrhetic acid 2. Of the glycosides 16, 24, and 25, with β-D-glucuronopyranosylglucopyranose as the sugar component, 16 and 24 were as cytoprotective as 1 and 2, whereas 25 showed no remarkable activity. From stereomodels of the glycosides these differences in activity were inferred to be due to the stereochemistries of the terminal β-D-glucuronopyranoses in the molecules. Glycoside 46, in which the terminal β-D-glucuronopyranose of 2 was replaced by β-D-galacturonopyranose, was as potent as 2. Further, it was confirmed that a free COOH group on the E ring of aglycon was essential for the activity.