89157-97-1

Basic information

• Product Name: 1,6-anhydro-2,3,4-tri-O-benzyl-β-L-idopyranose
• Synonyms: 1,6-anhydro-2,3,4-tri-O-benzyl-β-L-idopyranose
• CAS NO: 89157-97-1
• Molecular Weight: 432.516
• Mol File: 89157-97-1.mol

Chemical Properties

• CAS DataBase Reference: 1,6-anhydro-2,3,4-tri-O-benzyl-β-L-idopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-anhydro-2,3,4-tri-O-benzyl-β-L-idopyranose(89157-97-1)
• EPA Substance Registry System: 1,6-anhydro-2,3,4-tri-O-benzyl-β-L-idopyranose(89157-97-1)

Safety Data

• Hazardous Substances Data: 89157-97-1(Hazardous Substances Data)

Upstream product

• 641635-63-4 ((3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol 
• 100-39-0 benzyl bromide 
• 60619-47-8 1,6-anhydro-β-L-idopyranose 

Downstream Products

• 109914-80-9 methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-sulfo-3-O-(2,3,4-tri-O-benzyl-β-L-idopyranosyluronic acid)-β-D-galactopyranoside, disodium salt 
• 109914-80-9 methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-sulfo-3-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyluronic acid)-β-D-galactopyranoside, disodium salt 
• 109914-81-0 methyl 2-acetamido-2-deoxy-3-O-(β-L-idopyranosyluronic acid)-4-O-sulfo-β-D-galactopyranoside, disodium salt 
• 109914-74-1 methyl 2-azido-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-β-L-idopyranosyluronic acid)-β-D-galactopyranoside 
• 109914-70-7 methyl 2-azido-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyluronic acid)-β-D-galactopyranoside 
• 109914-69-4 Acetic acid (2R,3R,4R,5R,6R)-5-azido-2-benzyloxymethyl-6-methoxy-4-((2S,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 109914-68-3 methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyl)-β-D-galactopyranoside 
• 109914-84-3 methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-β-L-idopyranosyluronic acid)-β-D-galactopyranoside 
• 109914-78-5 methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyluronic acid)-β-D-galactopyranoside 
• 109914-83-2 methyl 2-acetamido-4-O-acetyl-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-β-L-idopyranosyl)-β-D-galactopyranoside 
• 109914-77-4 methyl 2-acetamido-4-O-acetyl-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyl)-β-D-galactopyranoside 
• 109914-79-6 methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-benzyl-α-L-idopyranuronate)-β-D-galactopyranoside 
• 120048-16-0 (3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-ol 
• 109914-65-0 2,3,4-tri-O-benzyl-1,6-di-O-chloroacetyl-L-idopyranose 

Relevant articles and documents

SYNTHESIS OF SOME ARYL 2,3,4,6-TETRA-O-ACETYL-L-IDOPYRANOSIDES AND OF 4-METHYLCOUMARIN-7-YL α-L-IDOPYRANOSIDURONIC ACID

Several routes for synthesis of 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-β-L-idofuranose have been evaluated.Previously described routes, which involved selective sulphonylation, were not reproducible on a 100-g scale.To overcome this difficulty, a new variation was developed, involving complete tosylation of 1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone followed by reduction and acetylation.The idofuranose derivative was converted into the desired 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose via 1,6-anhydro-β-L-idopyranose.Fusion of 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose with 4-nitrophenol, 1- or 2-naphtol, or 4-methylcoumarin-7-ol, using freshly fused zinc chloride as catalyst, gave an anomeric mixture of glycosides, with the α anomer being preponderant.The major 4-methylcoumarin-7-yl glycoside was deacylated and converted, by catalytic oxidation, into 4-methylcoumarin-7-yl α-L-idopyranosiduronic acid, fluorogenic substrate for α-L-iduronidase.

Probing the specificity of aminoglycoside-ribosomal RNA interactions with designed synthetic analogs

The binding of neomycin B and related aminoglycoside antibiotics to the prokaryotic ribosomal RNA decoding region has been investigated using a recently developed surface plasmon resonance assay. A number of naturally occurring aminoglycosides containing a neamine or neamine-like substructure bind specifically to a model of the site of the ribosomal decoding region RNA. This recognition event is the basis of the antibacterial activity of this class of compounds. A series of analogs was designed and synthesized to probe the role of neomycin ring IV (2,6-dideoxy-2,6-diamino-β-L- idopyranose). The binding results indicate that the positive charge presented on the idose ring is necessary for specific binding in vitro and cannot be replaced by amines attached via flexible linkers. However, the antibiotic activity (minimum inhibitory concentration) of the analog where ring IV is replaced with a diamine tail is the same as neomycin B in a liquid culture assay against Escherichia coli.