6207-76-7

Basic information

• Product Name: 2,3,4,6-Tetra-O-acetyl-a-D-glucopyranose
• Synonyms: 2,3,4,6-Tetra-O-acetyl-a-D-glucopyranose;2,3,4,6-Tetraacetyl-alpha-D-glucopyranose
• CAS NO: 6207-76-7
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.30
• Mol File: 6207-76-7.mol
• Article Data: 316

Chemical Properties

• Melting Point: 101-102 °C
• Boiling Point: 0.125 °C(Press: 0.001 Torr)
• Appearance: /
• Density: 1.33±0.1 g/cm3 (20 oC 760 Torr)
• PKA: 11.44±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-Tetra-O-acetyl-a-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-acetyl-a-D-glucopyranose(6207-76-7)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-acetyl-a-D-glucopyranose(6207-76-7)

Safety Data

• Hazardous Substances Data: 6207-76-7(Hazardous Substances Data)

Usage

General Description

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranose is a chemical compound commonly used as a protecting group in carbohydrate chemistry. It is a derivative of glucose, where the hydroxyl groups at positions 2, 3, 4, and 6 are acetylated. This modification protects the hydroxyl groups from participating in undesired reactions and allows for selective manipulation of other functional groups in the molecule. Additionally, the acetyl groups can be easily removed under mild conditions, making this compound a valuable tool in the synthesis of complex carbohydrates and glycoconjugates. Its application in carbohydrate research has made it an important building block in the field of organic chemistry.

Upstream product

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• 107-18-6 allyl alcohol 
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• 27851-29-2 benzyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 
• 3255-90-1 tetra-O-acetyl-N-p-tolyl-β-D-glucopyranosylamine 
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Downstream Products

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• 109922-74-9 Benzoic acid (2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 
• 109922-75-0 Benzoic acid (2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 
• 85249-43-0 allyl-β-D-mannopyranoside 
• 316382-36-2 allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-4-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 
• 316382-37-3 allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 
• 1314918-20-1 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl ortho-hexynylbenzoate 
• 1314918-19-8 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl ortho-hexynylbenzoate 
• 6605-40-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 439-01-0 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl fluoride 
• 1352278-39-7 (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 1352427-79-2 (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,3,4,6-tetra-O-benzoyl-β-D-mannopyranoside 
• 132153-84-5 2-O-(α-D-mannosyl)hydroxyethyl methacrylate 
• 10343-13-2 O-benzyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 

Relevant articles and documents

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.

First total syntheses of two natural glycosides

Isosyringinoside (1) and 3-(O-β-D-glucopyranosyl)-α-(O-β-D-glucopyranosyl)-4-hydroxy phenylethanol (2), the natural bioactive compounds contained unique structures, were first totally synthesized using easily available materials in short convenient routes with overall yields of 20.2% and 27.0%, respectively. An efficient total synthesis of 1 was developed in six steps, which contained two key steps of highly regioselective glycosylation without any selective protection steps. The seven-step synthesis of 2 involved two steps of regioselective glycosylations using BF3–O(C2H5)2 and TMSOTf as catalysts, respectively.

3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL

The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.