92052-29-4

Basic information

• Product Name: 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate
• Synonyms: 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate;2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl trichloroacetimidate;2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl 2,2,2-TrichloroacetiMidate;2,3,4,6-Tetra-O-acetyl-1-O-trichloroacetimidoyl-beta-D-glucopyranoside min. 99%;2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl trichloroacetimidate;-D-glucopyranosyl 2,2,2-Trichloroacetimidate;2,3,4,6-Tetra-O-acetyl-&beta
• CAS NO: 92052-29-4
• Molecular Formula: C₁₆H₂₀Cl₃NO₁₀
• Molecular Weight: 492.69
• Mol File: 92052-29-4.mol
• Article Data: 73

Chemical Properties

• Melting Point: 154.0 to 160.0 °C
• Boiling Point: 463.341°C at 760 mmHg
• Flash Point: 234.02°C
• Appearance: /
• Density: 1.558g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 1.39±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate(92052-29-4)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate(92052-29-4)

Safety Data

• Hazardous Substances Data: 92052-29-4(Hazardous Substances Data)

Usage

General Description

2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate is a chemical compound used in the synthesis of carbohydrates. It is commonly used as a protecting group for the hydroxyl groups in sugar molecules, allowing for selective reactions to take place in the presence of other functional groups. 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate is often utilized in the field of organic chemistry to modify and manipulate the structure of sugars, enabling the creation of complex carbohydrate molecules for various applications in drug development, food science, and materials research. Its unique chemical properties make it a valuable tool in the synthesis of complex carbohydrates and the study of their biological functions.

InChI:InChI=1/C16H20Cl3NO10/c1-6(21)25-5-10-11(26-7(2)22)12(27-8(3)23)13(28-9(4)24)14(29-10)30-15(20)16(17,18)19/h10-14,20H,5H2,1-4H3/t10-,11+,12-,13-,14-/m0/s1

Upstream product

• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 545-06-2 trichloroacetonitrile 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 630-18-2 tert-butyl isocyanide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 492-61-5 β-D-glucose 
• 604-68-2 α-D-glucopyranose peracetylate 
• 7296-64-2 β-D-galactopyranoside 
• 100-46-9 benzylamine 
• 4163-60-4 β-D-galactose peracetate 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 

Downstream Products

• 64044-49-1 3,4,6-Tri-O-acetyl-1,2-O-<1-(exo-cyclohexyloxy)ethylidene>-α-D-glucopyranose 
• 172276-07-2 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester 
• 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 
• 310882-75-8 5-[1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hexyn-6-yl]-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine 
• 1092840-34-0 methyl 2-acetamido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-O-benzyl-3-O-chloroacetyl-2-deoxy-β-D-glucopyranoside 
• 1030834-46-8 2-(phenyloxycarbonylthioxy)-3-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 1060659-71-3 2-(phenyloxycarbonylthioxy)-3-butenyl tetra-O-acetyl-β-D-galactopyranoside 
• 1192262-84-2 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-4-phenylethynyl-α-D-galactopyranoside 
• 1192262-83-1 methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-4-phenylethynyl-α-D-galactopyranoside 
• 1192262-89-7 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-4-trimethylsilylethynyl-α-D-galactopyranoside 
• 1192262-87-5 methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-4-trimethylsilylethynyl-α-D-galactopyranoside 
• 195976-08-0 N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-[O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-galactopyranosyl)-(1''-3)-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-L-threonine tert-butyl ester 
• 67909-25-5 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 6160-79-8 4-methylumbelliferyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 

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.

An alternative approach for the synthesis of sulfoquinovosyldiacylglycerol

Sulfoquinovosyldiacylglycerol (SQDG) is a glycolipid ubiquitously found in photosyn-thetically active organisms. It has attracted much attention in recent years due to its biological ac-tivities. Similarly, the increasing demand for vegan and functional foods has led to a growing interest in micronutrients such as sulfolipids and their physiological influence on human health. To study this influence, reference materials are needed for developing new analytical methods and providing enough material for model studies on the biological activity. However, the availability of these materials is limited by the difficulty to isolate and purify sulfolipids from natural sources and the unavailability of chemical standards on the market. Consequently, an alternative synthetic route for the comprehensive preparation of sulfolipids was established. Here, the synthesis of a sulfolipid with two identical saturated fatty acids is described exemplarily. The method opens possibilities for the preparation of a diverse range of interesting derivatives with different saturated and unsatu-rated fatty acids.