74808-10-9

Basic information

• Product Name: 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE
• Synonyms: α-D-Glucopyranose 2,3,4,6-Tetraacetate 1-(2,2,2-TrichloroethaniMidate);2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE;2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDIATE;O-(2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL)-TRICHLORACETIMIDATE
• CAS NO: 74808-10-9
• Molecular Formula: C₁₆H₂₀Cl₃NO₁₀
• Molecular Weight: 492.69
• Product Categories: Carbohydrates & Derivatives
• Mol File: 74808-10-9.mol
• Article Data: 115

Chemical Properties

• Melting Point: 66-68 °C
• Boiling Point: 463.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.55±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• PKA: 1.39±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE(74808-10-9)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE(74808-10-9)

Safety Data

• Hazardous Substances Data: 74808-10-9(Hazardous Substances Data)

Usage

Description

2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE is a chemical compound that serves as a key reagent in the synthesis of natural glycosides. It is characterized by its ability to facilitate the formation of glycosidic bonds, which are crucial in the construction of complex carbohydrate structures found in various natural products.

Uses

Used in Pharmaceutical Industry:
2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE is used as a synthetic reagent for the preparation of natural glycosides, such as Isosyringinoside and glucopyranosyl-glucopyranosyl-hydroxy phenylethanol I. These glycosides have potential applications in the development of pharmaceuticals, as they possess various biological activities and therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE is employed as a versatile building block for the construction of complex carbohydrate structures. Its ability to form stable glycosidic bonds makes it a valuable tool for the synthesis of oligosaccharides, polysaccharides, and other carbohydrate-containing compounds with potential applications in various industries, such as pharmaceuticals, cosmetics, and food.

Upstream product

• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 545-06-2 trichloroacetonitrile 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 83-87-4 D-glucose pentaacetate 
• 50-99-7 D-glucose 
• 492-61-5 β-D-glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 630-18-2 tert-butyl isocyanide 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 99701-73-2 3,4,6-Tri-O-acetyl-1,2-O-(4-oxo-4-phenyl-2-butyliden)-α-D-glucopyranose 
• 74808-17-6 methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 25546-57-0 dibenzyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phosphate 
• 94069-99-5 Benzoic acid (E)-(R)-1-[(S)-1-hexadecanoylamino-2-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 94069-99-5 (2S,3R)-N-palmitoyl-3-O-benzoyl-1-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-sphingosine 
• 34246-08-7 N-phenyl-2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosylamin 
• 113893-69-9 benzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(phenylamido)phosphate 
• 113893-63-3 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl diphenylphosphinate 
• 113893-64-4 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl phenylphosphonate 
• 150969-38-3 allyl 4-O-<4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl>-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 2530-07-6 tigogenyl acetate 
• 28154-24-7 O-β-tigogenyl glucoside tetraacetate 
• 122992-49-8 methyl 3,6-di-O-benzyl-2-(benzyloxycarbonylamino)-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 127473-30-7 1-methyl-2,3-diphenyl-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)indole 

Relevant articles and documents

PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS

The present invention relates to a synthesis process of β-6-sulfoquinovosyl-diacylglycerols. In particular, said process is for the synthesis of the compounds 1,2-O-distearoyl-3-O-(β- sulfoquinovosyl)-R/S-glycerol, 1,2-O-distearoyl-3-O-(β-sulfoquinovosyl)-R-glycerol or 1,2- O-distearoyl-3-O-(β-sulfoquinovosyl)-S-glycerol, named respectively Sulfavant A, Sulfavant R and Sulfavant S.

1,2,3,4-TETRAHYDROQUINOXALINE DERIVATIVE, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF

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Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides

N-Glycosyl N-sulfonyl amides have been synthesized by a self-promoted glycosylation, i. e. without any catalysts, promotors or additives. When the reactions were carried out at lower temperatures a mixture of N- and O-glycosides were observed, where the latter rearranged to give the β-N-glycosides at elevated temperatures. By this method sulfonylated asparagine derivatives can be selectively β-glycosylated in high yields by trichloroacetimidate glycosyl donors of different reactivity including protected glucosamine derivatives. The chemoselectivity in the glycosylations as well as the rearrangements from O-glycosides to β-N-glycosides gives information of the glycosylation mechanism. This method gives access to glycosyl sulfonyl amides under mild conditions.