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

Chemical Properties

Pale Yellow Low Melting Solid

Uses

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Trichloroacetimidate is a useful reagent for the synthesis of natural glycosides (Isosyringinoside and glucopyranosyL-?glucopyranosyl-?hydroxy phenylethanol I).

Upstream product

• 25878-60-8 D-galactose pentaacetate 
• 545-06-2 trichloroacetonitrile 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 492-61-5 β-D-glucose 
• 83-87-4 D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 604-69-3 β-D-glucose pentaacetate 
• 7296-64-2 β-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 10257-28-0 D-Galactose 
• 108-24-7 acetic anhydride 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 

Downstream Products

• 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 
• 113893-63-3 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl diphenylphosphinate 
• 141607-22-9 diphenyl (tetra-O-acetyl-α-D-glucopyranosyl) phosphate 
• 64044-49-1 3,4,6-Tri-O-acetyl-1,2-O-<1-(exo-cyclohexyloxy)ethylidene>-α-D-glucopyranose 
• 222425-32-3 benzyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-O-benzyl-3-O-phenoxycarbonyl-β-D-glucofuranosiduronamide 
• 259882-10-5 diosgenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-4,6-O-benzylidene-β-D-glucopyranoside 
• 259882-11-6 diosgenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-4,6-O-benzylidene-β-D-glucopyranoside 
• 260414-06-0 ethyl-2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)[2,3-b](11,12-benzo-1,4,7,10,13,16-hexaoxacyclooctadeca-11-ene)-2,3-dideoxy-α-D-glucopyranoside 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 273749-54-5 methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside 
• 314739-45-2 allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1-6)-2,3-di-O-benzyl-α-D-mannopyranoside 
• 500212-99-7 1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-lyxo-hex-1-enitol 
• 121358-45-0 (4-formyl-2-ethoxyphenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

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.

Synthesis of malformin-A1, C, a glycan, and an aglycon analog: Potential scaffolds for targeted cancer therapy

Improvement in therapeutic efficacy while reducing chemotherapeutic side effects remains a vital objective in synthetic design for cancer treatment. In keeping with the ethos of therapeutic development and inspired by the Warburg effect for augmenting biological activities of the malformin family of cyclic-peptide natural products, specifically anti-tumor activity, a β-glucoside of malformin C has been designed and synthesized utilizing precise glycosylation and solution phase peptide synthesis. We optimized several glycosylation procedures utilizing different donors and acceptors. The overarching goal of this study was to ensure a targeted delivery of a glyco-malformin C analog through the coupling of D-glucose moiety; selective transport via glucose transporters (GLUTs) into tumor cells, followed by hydrolysis in the tumor microenvironment releasing the active malformin C a glycon analog. Furthermore, total synthesis of malformin C was carried out with overall improved strategies avoiding unwanted side reactions thus increasing easier purification. We also report on an improved solid phase peptide synthesis protocol for malformin A1.

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.