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

• 19879-84-6 O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose 
• 100-44-7 benzyl chloride 
• 100-53-8 phenylmethanethiol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 18053-55-9 benzyl 2-(trimethylsilyl)ethyl sulfide 
• 15018-22-1 benzyl mercaptan zinc salt 
• 83-87-4 D-glucose pentaacetate 
• 67-64-1 acetone 
• 604-68-2 α-D-glucopyranose peracetylate 
• 100-39-0 benzyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 14204-26-3 N-(benzylthio)phthalimide 
• 1394124-53-8 S-benzyl 4-fluorobenzenesulfonothioate 

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 
• 158419-97-7 benzyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 1179891-90-7 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 216871-85-1 (2R,3R,4S,5R)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-[1-phenyl-meth-(Z)-ylidene]-tetrahydro-pyran 
• 216871-90-8 (2R,3S,4S,5R)-2-Hydroxymethyl-6-[1-phenyl-meth-(Z)-ylidene]-tetrahydro-pyran-3,4,5-triol 
• 216871-80-6 benzyl S,S-dioxo-1-thio-2,3,4,6-tetra-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 
• 437758-21-9 benzyl S,S-dioxo-1-thio-β-D-glucopyranoside 

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.

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.