197005-22-4

Basic information

• Product Name: Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside
• Synonyms: Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside;Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside;Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-&beta
• CAS NO: 197005-22-4
• Molecular Formula: C₂₁H₂₆O₈S
• Molecular Weight: 438.49
• Mol File: 197005-22-4.mol

Chemical Properties

• Melting Point: 113.0 to 117.0 °C
• Boiling Point: 533.22°C at 760 mmHg
• Flash Point: 258.678°C
• Appearance: /
• Density: 1.253g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.547
• CAS DataBase Reference: Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside(197005-22-4)
• EPA Substance Registry System: Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside(197005-22-4)

Safety Data

• Hazardous Substances Data: 197005-22-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside is used as a reagent in organic synthesis for the modification of sugar molecules. Its unique structure allows for the creation of various chemical derivatives, making it a valuable tool in the development of new compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside is used as a building block for the development of new drugs. Its ability to modify sugar molecules can contribute to the creation of innovative pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Industry:
Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside is also utilized in the agrochemical industry for the development of new agrochemical products. Its potential applications in this field can lead to the creation of more effective and environmentally friendly solutions for agriculture.
Used in Research and Development:
In research and development, Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside serves as a key compound for studying the properties and reactions of glycosides. Its unique structure and reactivity make it an important subject for scientific investigation, contributing to the advancement of knowledge in the field of chemistry.

InChI:InChI=1/C21H26O8S/c1-5-11-25-19-18(27-14(3)23)17(12-26-13(2)22)29-21(20(19)28-15(4)24)30-16-9-7-6-8-10-16/h5-10,17-21H,1,11-12H2,2-4H3/t17-,18+,19-,20?,21-/m0/s1

Upstream product

• 39698-00-5 acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 
• 108-98-5 thiophenol 

Downstream Products

• 1237530-78-7 C₂₁H₂₆O₉S 
• 556039-04-4 N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 556039-09-9 Succinic acid mono-[(2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl] ester 
• 556039-02-2 phenyl 3-O-allyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside 
• 556039-05-5 phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 197005-23-5 phenyl 3-O-allyl-1-thio-β-D-glucopyranoside 

Relevant articles and documents

D-glucose as a regioselectively addressable scaffold for combinatorial chemistry on solid phase

D-Glucose derivatives bearing an anomeric thiophenyl group and orthogonally protections on secondary hydroxyl groups were linked to solid supports (PS/DV polymer, tentagel resin) through an ester bond on C-6. It was investigated the possibility to remove orthogonally protecting groups and functionalize selectively the free hydroxyls groups and the anomeric carbon of sugars in solid phase.

Carbohydrate-based scaffolds for the generation of sortiments of bioactive compounds

The polyfunctionality and conformational rigidity of carbohydrates make this class of compounds ideal scaffolds for the production of sortiments1 of bioactive compounds. Examples of carbohydrate-derived peptidomimetics of biological interest, such as somatostatin agonists and integrin antagonists, are presented. In order to have access to solid phase supported sortiments of compounds, orthogonally protected or unprotected carbohydrates were linked to polymers and reacted in the solid phase employing different regioselective strategies. Original bicyclic and tricyclic glycidic scaffolds were easily obtained starting from natural sugars such as D-arabinose and D-fructose. Manipulation of these conformationally blocked compounds afforded different carbohydrate-based derivatives, among which azidoacids are useful precursors of β-turn peptidomimetics.