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

Chemical Properties

Pale Yellow Oil

Uses

Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside (cas# 18031-51-1) is a compound useful in organic synthesis.

Upstream product

• 850848-12-3 methyl 2,3,4-tri-3-O-acetyl-6-O-[2-(prenyloxymethyl)benzoyl]-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 29868-42-6 methyl 2,3-di-O-acetyl-α-D-glucopyranoside 
• 7432-72-6 methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose 
• 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 
• 75-36-5 acetyl chloride 
• 97-30-3 methyl-alpha-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 

Downstream Products

• 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 
• 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 
• 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.