162061-34-9

Basic information

• Product Name: METHYLMERCAPTO-2,3,4,6-TETRA-O-BENZYL-D-MANNOPYRANOSIDE
• Synonyms: METHYLMERCAPTO-2,3,4,6-TETRA-O-BENZYL-D-MANNOPYRANOSIDE
• CAS NO: 162061-34-9
• Molecular Formula: C35H38O5S
• Molecular Weight: 570.74
• Mol File: 162061-34-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 682.4°Cat760mmHg
• Flash Point: 366.5°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.618
• CAS DataBase Reference: METHYLMERCAPTO-2,3,4,6-TETRA-O-BENZYL-D-MANNOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLMERCAPTO-2,3,4,6-TETRA-O-BENZYL-D-MANNOPYRANOSIDE(162061-34-9)
• EPA Substance Registry System: METHYLMERCAPTO-2,3,4,6-TETRA-O-BENZYL-D-MANNOPYRANOSIDE(162061-34-9)

Safety Data

• Hazardous Substances Data: 162061-34-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C35H38O5S/c1-41-35-34(39-25-30-20-12-5-13-21-30)33(38-24-29-18-10-4-11-19-29)32(37-23-28-16-8-3-9-17-28)31(40-35)26-36-22-27-14-6-2-7-15-27/h2-21,31-35H,22-26H2,1H3/t31-,32-,33+,34+,35-/m1/s1

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 624-92-0 Dimethyldisulphide 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 17314-34-0 Dibutyl-bis-methylmercapto-zinn 
• 4163-60-4 β-D-galactose peracetate 
• 55722-48-0 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 160636-38-4 per-O-benzylated methyl α-thiogalactopyranoside 
• 100-39-0 benzyl bromide 
• 155-30-6 methyl 1-thio-β-D-galactopyranoside 
• 13350-45-3 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 30760-09-9 methyl 1-deoxy-1-thio-β-D-glucopyranoside 
• 66965-73-9 sodium salt of 1-thio-α-D-mannose 
• 7447-60-1 methyl 1-thio-β-D-mannopyranoside 

Downstream Products

• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 160636-38-4 per-O-benzylated methyl α-thiogalactopyranoside 
• 146453-40-9 O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-D-galactopyranosyl fluoride 
• 246516-65-4 O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl azide 
• 140420-82-2 O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 144069-06-7 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-galactopyranoside 
• 144069-05-6 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 

Relevant articles and documents

Anodic Reactivity of Alkyl S-Glucosides

A voltammetric study of a series of alkyl and aryl S-glucosides unveiled the reactivity patterns of alkyl S-glucosides toward anodic oxidation and found noteworthy differences with the trends followed by aryl derivatives. The oxidation potential of alkyl S-glucosides, estimated herein from square-wave voltammetry peak potentials (Ep), depends on the steric properties of the aglycone. Glucosides substituted with bulky groups exhibit Ep values at voltages more positive than the values of those carrying small aglycones. This relationship, observed in all analyzed alkyl series, is evidenced by good linear correlations between Ep and Taft's steric parameters (ES) of the respective alkyl substituents. Moreover, the role of the aglycone's steric properties as a primary reactivity modulator is backed by poor correlations between Ep and the radical stabilization energies (RSEs) of the aglycone-derived thiyl radicals (RS?). In contrast, aryl glucosides' Ep values exhibit excellent correlations with the aryl substituents' Hammett parameters (σ+) and the ArS?RSEs, evidencing the inherent stability of the reactive radical intermediate as the primary factor controlling aryl glucoside's electrochemical reactivity. The reactivity differences between alkyl and aryl S-glucosides also extend to the protective group's effect on Ep. Alkyl S-glucosides' reactivity proved to be more sensitive to protective group exchange.

Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions

Rate acceleration of O-glycosylation had been observed in p-xylene under frozen conditions, when thioglycosides were activated by methyl trifluoromethane sulfonate. Curiously, significant perturbation of stereoselectivity was observed. Effects of various

A new route to exo-glycals using the Ramberg-Baecklund rearrangement

A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Baecklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.