148888-66-8

Basic information

• Product Name: 1,2-anhydro-3,4,6-tri-O-benzyltalopyranose
• Synonyms: 1,2-anhydro-3,4,6-tri-O-benzyltalopyranose
• CAS NO: 148888-66-8
• Molecular Formula: C₂₇H₂₈O₅
• Molecular Weight: 432.50822
• Mol File: 148888-66-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 560.3°Cat760mmHg
• Flash Point: 222.9°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 5.23E-12mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: 1,2-anhydro-3,4,6-tri-O-benzyltalopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-anhydro-3,4,6-tri-O-benzyltalopyranose(148888-66-8)
• EPA Substance Registry System: 1,2-anhydro-3,4,6-tri-O-benzyltalopyranose(148888-66-8)

Safety Data

• Hazardous Substances Data: 148888-66-8(Hazardous Substances Data)

Usage

Type of compound

Talopyranose, a rare carbohydrate

Structure

Contains a talopyranose ring with three benzyl groups attached

Use

Building block in organic synthesis

Versatility

Can be used to create complex molecules and various derivatives

Importance

Unique structure and reactivity make it significant in organic chemistry research and pharmaceutical development

Applications

Potential use in various fields of science and industry

InChI:InChI=1/C27H28O5/c1-4-10-20(11-5-1)16-28-19-23-24(29-17-21-12-6-2-7-13-21)25(26-27(31-23)32-26)30-18-22-14-8-3-9-15-22/h1-15,23-27H,16-19H2/t23-,24+,25+,26+,27+/m1/s1

Upstream product

• 65827-59-0 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Downstream Products

• 83861-83-0 (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-3-tert-butoxy-2-methyl-propyl)-tetrahydro-pyran-3-ol 
• 136824-11-8 methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 88405-94-1 1,2:5,6-di-O-isopropylidene-3-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucofuranose 
• 112330-08-2 (2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)glycerol 
• 83861-83-0 (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-tert-butoxy-2-methyl-propyl)-tetrahydro-pyran-3-ol 
• 83861-83-0 (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-3-tert-butoxy-2-methyl-propyl)-tetrahydro-pyran-3-ol 

Relevant articles and documents

Synthesis and Conformational Analysis of 2-O-Silyl Protected Nucleosides from Unprotected Nucleobases and Sugar Epoxides

Synthesis of orthogonally protected 2-silyl nucleosides were achieved by trans opening of sugar epoxides with nucleobases catalyzed by trimethylsilyltrifluoromethanesulfonate using hexamethyldisilazane both as solvent and silylating agent. Both α and β nu

Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups

In this article, we evaluate glycosyl dithiocarbamates (DTCs) with unprotected C2 hydroxyls as donors in β-linked oligosaccharide synthesis. We report a mild, one-pot conversion of glycals into β-glycosyl DTCs via DMDO oxidation with subsequent ring opening by DTC salts, which can be generated in situ from secondary amines and CS2. Glycosyl DTCs are readily activated with Cu(I) or Cu(II) triflate at low temperatures and are amenable to reiterative synthesis strategies, as demonstrated by the efficient construction of a tri-β-1,6-linked tetrasaccharide. Glycosyl DTC couplings are highly β-selective despite the absence of a preexisting C2 auxiliary group. We provide evidence that the directing effect is mediated by the C2 hydroxyl itself via the putative formation of a cis-fused bicyclic intermediate.

Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides

Glycals and 4-deoxypentenosides (4-DPs), unsaturated pyranosides with similar structures and reactivity profiles, can exhibit a high degree of stereoselectivity upon epoxidation with dimethyldioxirane (DMDO). In most cases, the glycals and their corresponding 4-DP isosteres share the same facioselectivity, implying that the pyran substituents are largely responsible for the stereodirecting effect. Fully substituted dihydropyrans are subject to a "majority rule", in which the epoxidation is directed toward the face opposite to two of the three groups. Removing one of the substituents has a variable effect on the epoxidation outcome, depending on its position and also on the relative stereochemistry of the remaining two groups. Overall, we observe that the greatest loss in facioselectivity for glycals and 4-DPs is caused by removal of the C3 oxygen, followed by the C5/anomeric substituent, and least of all by the C4/C2 oxygen. DFT calculations based on polarized-π frontier molecular orbital (PPFMO) theory support a stereoelectronic role for the oxygen substituents in 4-DP facioselectivity, but less clearly so in the case of glycals. We conclude that the anomeric oxygen in 4-DPs contributes toward a stereoelectronic bias in facioselectivity whereas the C5 alkoxymethyl in glycals imparts a steric bias, which at times can compete with the stereodirecting effects from the other oxygen substituents.