6612-63-1

Basic information

• Product Name: .beta.-D-Glucopyranoside, phenylmethyl 1-thio-, tetraacetate
• Synonyms: .beta.-D-Glucopyranoside, phenylmethyl 1-thio-, tetraacetate
• CAS NO: 6612-63-1
• Molecular Formula: C₂₁H₂₆O₉S
• Molecular Weight: 454.4907
• Mol File: 6612-63-1.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 526°Cat760mmHg
• Flash Point: 252.6°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 3.73E-11mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: .beta.-D-Glucopyranoside, phenylmethyl 1-thio-, tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Glucopyranoside, phenylmethyl 1-thio-, tetraacetate(6612-63-1)
• EPA Substance Registry System: .beta.-D-Glucopyranoside, phenylmethyl 1-thio-, tetraacetate(6612-63-1)

Safety Data

• Hazardous Substances Data: 6612-63-1(Hazardous Substances Data)

Usage

General Description

.beta.-D-Glucopyranoside, phenylmethyl 1-thio-, tetraacetate is a chemical compound that is derived from glucopyranoside, a type of sugar. It is commonly used as a protecting group for the functional group of sugars to prevent unwanted reactions during chemical synthesis. The phenylmethyl 1-thio group provides stability and protection to the sugar molecule, while the tetraacetate moieties add further protection. .beta.-D-Glucopyranoside, phenylmethyl 1-thio-, tetraacetate is often used in organic synthesis, particularly in the production of pharmaceuticals and other fine chemicals.

InChI:InChI=1/C21H26O9S/c1-12(22)26-10-17-18(27-13(2)23)19(28-14(3)24)20(29-15(4)25)21(30-17)31-11-16-8-6-5-7-9-16/h5-9,17-21H,10-11H2,1-4H3

Upstream product

• 14204-26-3 N-(benzylthio)phthalimide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 1394124-53-8 S-benzyl 4-fluorobenzenesulfonothioate 
• 16601-01-7 benzenethiosulfonic acid S-benzyl ester 
• 16601-02-8 S-benzyl 4-methylbenzenethiosulfonate 
• 7559-62-8 S-benzyl methanethiosulfonate 
• 19879-84-6 tetraacetyl thioglucose 
• 100-39-0 benzyl bromide 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 100-53-8 phenylmethanethiol 
• 63783-77-7 2,3,4,6-tetra-O-acetyl-glucosylthioacetate 
• 72541-16-3 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 70569-27-6 benzyl 1-thio-β-D-glucopyranoside 

Downstream Products

• 216871-75-9 benzyl S,S-dioxo-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 70569-27-6 benzyl 1-thio-β-D-glucopyranoside 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 623148-72-1 2,6-anhydro-1-phenyl-1-keto-4-O-methyl-7-deoxy-α-D-altro-heptitol 
• 623148-70-9 (1R)-2,6-anhydro-1-phenyl-4-O-methyl-7-deoxy-α-D-altro-heptitol 
• 623148-65-2 (1R)-2,6-anhydro-1-phenyl-4-O-methyl-α-D-altro-heptitol 
• 623148-69-6 (1R)-2,6-anhydro-1-phenyl-4-O-methyl-7-deoxy-7-iodo-α-D-altro-heptitol 
• 623148-34-5 (2S)-methyl 3,7-anhydro-2-phenyl-5-O-methyl-8-deoxy-α-D-altro-octitolate 
• 623148-33-4 (2R)-methyl 3,7-anhydro-2-phenyl-5-O-methyl-8-deoxy-α-D-altro-octitolate 
• 623148-68-5 (1R)-2,6-anhydro-1-phenyl-1-O-[2-(trimethylsilyl)ethoxymethyl]-4-O-methyl-7-deoxy-α-D-altro-heptitol 
• 623148-67-4 (1R)-2,6-anhydro-1-phenyl-1-O-[2-(trimethylsilyl)ethoxymethyl]-4-O-methyl-7-deoxy-7-iodo-α-D-altro-heptitol 
• 623148-64-1 (1R)-2,6-anhydro-1-phenyl-1-O-[2-(trimethylsilyl)ethoxymethyl]-4-O-methyl-α-D-altro-heptitol 
• 623148-73-2 2,6-anhydro-1-phenyl-1-keto-3,5-bis-O-tert-butyldimethylsilyl-4-O-methyl-7-deoxy-α-D-altro-heptitol 
• 623148-74-3 3,7-anhydro-1,2,8-trideoxy-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-α-D-altro-oct-1-enitol 

Relevant articles and documents

Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions

A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.

Photochemical Functionalization of Heterocycles with EBX Reagents: C?H Alkynylation versus Deconstructive Ring Cleavage**

The development of novel methodologies for the functionalization of saturated heterocycles is highly desirable. Herein, we report a cheap and efficient photochemical method for the C?H functionalization of saturated O-heterocycles, as well as the deconstructive ring-cleavage of S-heterocycles, employing hypervalent iodine alkynylation reagents (ethynylbenziodoxolones, EBX). This photochemical alkynylation is performed utilizing phenylglyoxylic acid as the photoinitiator, leading to the corresponding products in good to high yields, under household fluorescent light bulb irradiation. When O-heterocycles were employed, the expected α-C?H alkynylation took place. In contrast, oxidative ring-opening to form a thioalkyne and an aldehyde was observed with S-heterocycles. Preliminary mechanistic experiments are presented to give first insights into this puzzling divergent reactivity.

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.