22855-03-4

Basic information

• Product Name: 2,3-Dihydro-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-indole
• Synonyms: 2,3-Dihydro-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-indole
• CAS NO: 22855-03-4
• Molecular Formula: C22H27NO9
• Molecular Weight: 449.4511
• Mol File: 22855-03-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 537.4 °C at 760 mmHg
• Flash Point: 278.8 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 1.28E-11mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 2,3-Dihydro-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dihydro-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-indole(22855-03-4)
• EPA Substance Registry System: 2,3-Dihydro-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-indole(22855-03-4)

Safety Data

• Hazardous Substances Data: 22855-03-4(Hazardous Substances Data)

Usage

General Description

2,3-Dihydro-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-indole, also known as tetraacetylindolylglucopyranoside, is a complex chemical compound consisting of a glucopyranosyl group attached to an indole ring. It is commonly used in organic synthesis and chemical research as a versatile building block for creating various indole and sugar derivatives. The tetraacetyl-β-D-glucopyranosyl group serves to protect the reactive hydroxyl groups of the glucose ring, allowing for selective manipulation of the molecule's structure. 2,3-Dihydro-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-indole has potential applications in the pharmaceutical industry as a starting material for the synthesis of bioactive compounds and drug development.

InChI:InChI=1/C22H27NO9/c1-12(24)28-11-18-19(29-13(2)25)20(30-14(3)26)21(31-15(4)27)22(32-18)23-10-9-16-7-5-6-8-17(16)23/h5-8,18-22H,9-11H2,1-4H3

Upstream product

• 108-24-7 acetic anhydride 
• 496-15-1 1-indoline 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 
• 39264-64-7 1-(β-D-glucopyranosyl)indoline 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 5059-38-1 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1H-indole 
• 1493759-80-0 3-(4-cyclopentylphenylmethyl)-1-(β-D-glucopyranosyl)indole 
• 1493759-13-9 C₃₄H₃₇NO₁₀ 
• 1493759-35-5 C₃₂H₃₅NO₉ 
• 1493759-38-8 C₃₃H₃₇NO₉ 
• 1493759-41-3 C₃₄H₃₉NO₉ 
• 1452838-63-9 3-(4-cyclopropylphenylmethyl)-1-(β-D-glucopyranosyl)indole 
• 1493759-79-7 3-(4-cyclobutylphenylmethyl)-1-(β-D-glucopyranosyl)indole 

Relevant articles and documents

Synthesis of 1,3- and 2,3-diglycosylated indoles as potential trisaccharide mimetics

Diglycosylated heteroaromatics may serve as metabolically stable mimetics of trisaccharides. Herein, the preparation of several 1,3- and 2,3-diglycosylindoles by direct C-glycosylation of monoglycosylated precursors is described. Georg Thieme Verlag Stuttgart ? New York.

Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives

In the course of structure-activity relationship studies, diversely substituted 1-(β-D-glucopyranosyl)-isoindigo derivatives were prepared from commercially available indolines. Their antiproliferative activities were evaluated toward a panel of human solid cancer cell lines (PC 3, DLD-1, MCF-7, M4Beu, A549, PA 1), a murine cell line (L929) and a human fibroblast primary culture to get an insight into the substitution pattern required for the best biological potencies.