3254-16-8

Basic information

• Product Name: 3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSE 1,2-(METHYL ORTHOACETATE)
• Synonyms: α-D-Glucopyranose, 1,2-O-(1-Methoxyethylidene)-3,4,6-triacetate;3,4,6-Tri-O-acetyl-a-D-glucopyranose1,2-(methylorthoacetate);3,4,6-Tri-O-acetyl-α-D-glucopyranose-1,2-(methyl orthoacetate);a-D-Glucopyranose,1,2-O-(1-methoxyethylidene)-, triacetate (9CI)
• CAS NO: 3254-16-8
• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 362.329
• EINECS: 1533716-785-6
• Mol File: 3254-16-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 419.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSE 1,2-(METHYL ORTHOACETATE)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSE 1,2-(METHYL ORTHOACETATE)(3254-16-8)
• EPA Substance Registry System: 3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSE 1,2-(METHYL ORTHOACETATE)(3254-16-8)

Safety Data

• Hazardous Substances Data: 3254-16-8(Hazardous Substances Data)

Usage

General Description

3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSE 1,2-(METHYL ORTHOACETATE) is a chemical compound that is formed by the acetylation of alpha-D-galactopyranose, specifically at the 3, 4, and 6 hydroxyl groups. Additionally, a methyl orthoacetate group is attached to the 1 and 2 positions of the galactopyranose molecule. 3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSE 1,2-(METHYL ORTHOACETATE) is commonly used as a building block in organic synthesis and as a protecting group for the hydroxyl groups of galactopyranose in carbohydrate research. It is a white, crystalline substance that is sparingly soluble in water and ethanol.

Upstream product

• 529493-92-3 2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1067-52-3 tributyltin methoxide 
• 67-56-1 methanol 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 66118-22-7 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-isocyanotetrahydro-2H-pyran-3,4,5-triyl triacetate 

Downstream Products

• 169106-94-9 2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl fluoride 
• 57884-82-9 2,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 22860-22-6 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose 
• 18968-05-3 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 79218-91-0 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-6-O-trityl-β-D-mannopyramose 
• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 250734-70-4 ((3aR,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-5-ylmethoxy)-tert-butyl-dimethyl-silane 
• 289653-64-1 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl bromide 
• 280574-35-8 [(2S,3R,4S,5R,6R)-4,5-Bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-2-phenylselanyl-tetrahydro-pyran-3-yloxy]-((3aR,5S,6aR)-2,2-dimethyl-6-methylene-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-dimethyl-silane 
• 280574-32-5 phenyl 3,4,6-tri-O-p-methoxybenzyl-1-seleno-β-D-glucopyranoside 
• 280574-39-2 3,4,6-tri-O-p-methoxybenzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 

Relevant articles and documents

Combinatorial synthesis of an oligosaccharide library by using β-bromoglycoside-mediated iterative glycosylation of selenoglycosides: Rapid expansion of molecular diversity with simple building blocks

A new method for constructing an oligosaccharide library composed of structurally defined oligosaccharides is presented based on an iterative glycosylation of selenoglycosides. Treatment of 2-acyl-protected selenoglycosides with bromine selectively generates β-bromoglycosides, which serve as glycosyl cation equivalents in the oligosaccharide synthesis. Thus, the coupling of the bromoglycosides with another selenoglycoside affords the corresponding glycosylated selenoglycosides, which can be directly used to next glycosylation. The iteration of this sequence allows the synthesis of a variety of oligosaccharides including an elicitor active heptasaccharide. A characteristic feature of the iterative glycosylation is that glycosyl donors and acceptors with the same anomeric reactivity can be selectively coupled by activation of the glycosyl donor prior to coupling with the glycosyl acceptor. Therefore, same selenoglycosides can be used for both the glycosyl donors and the acceptors. This feature has been exemplified by a construction of an oligosaccharide library directed to elicitor-active oligosaccharides. The library composed of stereochemically defined oligoglucosides with considerable structural diversity can be constructed starting from simple selenoglycosides.

Reaction des glycosyl isonitriles avec les amines et les alcools

After complexation with metals, glycosylisonitriles 1 react with alcohols to give mainly orthoesters, if C-2 bears a participating group, and/or alkyl glycosides without particular stereoselectivity.In the case of amines, formamidines are obtained by α-addition to 1 in good yields.An example of further heterocyclisation is given with the stereospecific synthesis of the glucosylquinazolinone 15.