22855-03-4

Usage

Uses

Used in Organic Synthesis:
2,3-Dihydro-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-indole is utilized as a key intermediate in organic synthesis, particularly for the production of various indole and sugar derivatives. Its protected structure allows for selective reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3-Dihydro-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-indole serves as a starting material for the synthesis of bioactive compounds. Its unique structure and reactivity make it a promising candidate for drug development, potentially leading to the discovery of new therapeutic agents.
Used in Chemical Research:
2,3-Dihydro-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-indole is also employed in chemical research as a model compound for studying the properties and reactions of indole and sugar-containing molecules. Its protected structure provides a controlled environment for investigating the reactivity and selectivity of various chemical processes.

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

• 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 
• 5059-38-1 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1H-indole 

Relevant academic research and scientific papers

Novel indole-N-glucoside, TA-1887 As a sodium glucose cotransporter 2 inhibitor for treatment of type 2 diabetes

Inhibition of the renal sodium glucose cotransporter (SGLT) increases urinary glucose excretion (UGE) and thus reduces blood glucose levels during hyperglycemia. To explore the potential of new antihyperglycemic agents, we synthesized and determined the h

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.

Sweet (hetero)aromatics: Glycosylated templates for the construction of saccharide mimetics

Mono- and diglycosylated aromatics and heteroaromatics may serve as building blocks for the construction of metabolically stable mimetics of oligosaccharides. Methods for their preparation from monosaccharidic precursors by direct C-glycosylation, dipolar cycloaddition or Larock cyclization are described.

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.

Synthesis of 1-glycosyl derivatives of benzocamalexin

The linear synthesis of 1-(β-o-glucopyranosyl)-, 1-(β-D- galactopyranosyl)-, 1-(β-D-mannopyranosyl)- and 1-(β-D-ribofuranosyl) benzocamalexin was elaborated from indoline as a starting compound and corresponding pentaacetylhexoses or 1-O-acetyl-2,3,5-tri-