18031-51-1

Basic information

• Product Name: Methyl2,3,6-tri-O-acetyl-a-D-glucopyranoside
• Synonyms: Methyl α-D-Glucopyranoside 2,3,6-Triacetate
• CAS NO: 18031-51-1
• Molecular Formula: C₁₃H₂₀O₉
• Molecular Weight: 0
• Mol File: 18031-51-1.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl2,3,6-tri-O-acetyl-a-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl2,3,6-tri-O-acetyl-a-D-glucopyranoside(18031-51-1)
• EPA Substance Registry System: Methyl2,3,6-tri-O-acetyl-a-D-glucopyranoside(18031-51-1)

Safety Data

• Hazardous Substances Data: 18031-51-1(Hazardous Substances Data)

Usage

Description

Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside, with the chemical name CAS# 18031-51-1, is a derivative of α-D-glucopyranoside, a monosaccharide. It is characterized by the presence of three acetyl groups attached to the 2nd, 3rd, and 6th positions of the glucopyranose ring, which gives it unique chemical properties. This pale yellow oil is a versatile compound used in various organic synthesis processes.

Uses

Used in Organic Synthesis:
Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows for selective reactions and modifications, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside is used as a starting material for the synthesis of glycosides and other carbohydrate-based drugs. Its ability to form stable glycosidic linkages with various aglycones makes it an essential component in the development of new therapeutic agents with improved pharmacokinetic properties.
Used in Agrochemical Industry:
Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside is also utilized in the agrochemical industry for the synthesis of glycosylated pesticides and other bioactive compounds. The introduction of carbohydrate moieties can enhance the solubility, stability, and bioavailability of these agrochemicals, leading to more effective and environmentally friendly products.
Used in Specialty Chemicals:
In the specialty chemicals sector, Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside is employed as a precursor for the synthesis of various functional materials, such as surfactants, polymers, and coatings. Its unique chemical properties enable the development of innovative products with tailored properties for specific applications.

Upstream product

• 29868-42-6 methyl 2,3-di-O-acetyl-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 75-36-5 acetyl chloride 
• 7432-72-6 methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose 
• 850848-12-3 methyl 2,3,4-tri-3-O-acetyl-6-O-[2-(prenyloxymethyl)benzoyl]-α-D-glucopyranoside 
• 56-35-9 bis(tri-n-butyltin)oxide 
• 131021-83-5 methyl 6-O-formyl-α-D-glucopyranoside 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 7511-40-2 methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside 
• 428500-98-5 methyl 2,3,4-tri-O-acetyl-6-O-[(2-azidomethyl)phenylacetyl]-α-D-glucopyranoside 
• 81712-51-8 methyl 2,3,6-tri-O-acetyl-4-O-diphenylmethyl-α-D-glucopyranoside 
• 131000-31-2 methyl 2,3,4-tri-O-acetyl-6-O-formyl-α-D-glucopyranoside 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 

Downstream Products

• 1095481-08-5 methyl 2,3-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside 
• 1095480-56-0 methyl 2,3-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-α-D-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside 
• 1200440-74-9 C₂₃H₃₀NO₁₂P 
• 1095480-92-4 methyl 2,3-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-α-L-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside 
• 1095481-27-8 methyl 2,3-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-β-L-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside 
• 81712-52-9 methyl 4-O-diphenylmethyl-2,3,6-tri-O-methyl-α-D-glucopyranoside 
• 365418-08-2 methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-C-((3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl)-2-propene)-α-D-glucopyranoside 
• 365418-10-6 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ol 
• 365418-07-1 methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-C-((3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl)-(2-ethanoate))-α-D-glucopyranoside 
• 365418-09-3 (2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-3,4-dihydro-2H-pyran 
• 557088-28-5 methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside 
• 224324-88-3 methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanoic acid)-α-D-glucopyranoside 
• 365418-30-0 methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside 
• 32934-08-0 methyl 2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-α-D-galactopyranoside 

Relevant articles and documents

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An improved synthesis of 4-deoxy-4-fluoro-D-galactopyranosyl derivatives

This note presents an improved synthesis of 4-deoxy-4-fluoro-D-galactopyranosyl derivatives, using a sterically unencumbered acylating agent such as acetyl chloride.

2-(Prenyloxymethyl)benzoyl (POMB) group: a new temporary protecting group removable by intramolecular cyclization

2-(Prenyloxymethyl)benzoates can be prepared from alcohols and readily available 2-(prenyloxymethyl)benzoic acid by standard acylation techniques or by Mitsunobu reaction with inversion of configuration. The POMB group can be cleaved first by oxidative removal of the prenyl group with DDQ followed by lactonization with expulsion of the alcohol catalyzed by Yb(OTf)3. These reaction conditions are compatible with the presence of a large number of common protecting groups.

Removal of acid-labile protecting groups on carbohydrates using water-tolerant and recoverable vanadyl triflate catalyst

Acetal, trityl, and TBDMS protecting groups on saccharides were subjected to alcoholysis using a catalytic amount of vanadyl triflate in an MeOH-CH 2Cl2 solvent system. The configuration at the anomeric positions of saccharides was retained, and no glycosidic bond cleavage and oxidation of sulfides were observed. The presented method was easily implemented, compatible with diverse functional groups, and regioselective in some cases.