74948-73-5

Basic information

• Product Name: Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-a-D-mannopyranoside
• Synonyms: Methyl 4,6-O-(1-Methylethylidene)-a-D-mannopyranoside Cyclic Carbonat;Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside;Methyl 4,6-O-(1-Methylethylidene)-α-D-mannopyranoside Cyclic Carbonate;Methyl 4,6-O-(1-Methylethylidene)-a-D-mannopyranoside Cyclic Carbonate
• CAS NO: 74948-73-5
• Molecular Formula: C11H16O7
• Molecular Weight: 0
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 74948-73-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Solubility: Methanol
• CAS DataBase Reference: Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-a-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-a-D-mannopyranoside(74948-73-5)
• EPA Substance Registry System: Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-a-D-mannopyranoside(74948-73-5)

Safety Data

• Hazardous Substances Data: 74948-73-5(Hazardous Substances Data)

Usage

Description

Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside is a white crystalline solid that serves as a key intermediate in the synthesis of α-mannosides. It is a complex carbohydrate derivative with unique chemical properties that make it valuable in various applications.

Uses

Used in Pharmaceutical Industry:
Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside is used as a synthetic intermediate for the production of α-mannosides, which are essential in the development of various pharmaceutical compounds. These α-mannosides play a crucial role in the design and synthesis of drugs targeting specific biological receptors, making them valuable in the treatment of various diseases.
Used in Chemical Research:
As a white crystalline solid with unique chemical properties, Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside is also used in chemical research for the investigation of carbohydrate chemistry, glycobiology, and the development of new synthetic methods and techniques.
Used in Synthesis of α-Mannosides:
Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside is used as a key building block for the synthesis of α-mannosides, which are important in the development of new drugs and pharmaceutical compounds. The synthesis of these complex carbohydrates is essential for understanding their biological functions and potential applications in medicine.

Upstream product

• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 63167-67-9 methyl 4,6-O-isopropylidene-α-D-mannopyranoside 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 79-22-1 methyl chloroformate 
• 74948-68-8 methyl 4,6-O-isopropylidene-2,3-O-thiocarbonyl-α-D-mannoside 
• 33842-02-3 dichloromethylenedimethyliminium chloride 

Downstream Products

• 53958-21-7 4,6-di-O-acetyl-2,3-O-carbonyl-α-D-mannopyranosyl bromide 
• 15814-59-2 (2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 53958-20-6 1,4,6-tri-O-acetyl-2,3-O-carbonyl-α-D-mannopyranose 
• 103559-62-2 1,4,6-tri-O-acetyl-2,3-O-carbonyl-β-D-mannopyranose 

Relevant articles and documents

The Reaction of N-Dichloromethylene-N,N-dimethylammonium Chloride (Viehe's Salt) with Some Carbohydrate Diols

The reaction of Viehe's salt (Me2N1+=CCl2Cl1-) with various carbohydrate diols (manno, allo) in the presence of a base is reported, the products being, after hydrolysis, either carbonate (with pyridine) or the carbamate (with triethylamine).A rationalization of the two different types of product formed is given in terms of the stereoelectronic control proposal by Deslongchamps.

The Reaction of Methyl 4,6-O-Isopropylidene-2,3-O-thiocarbonyl-α-D-mannoside with Methyl Iodide: a Synthesis of Methyl α-Tyveloside (Methyl 3,6-Dideoxy-α-D-arabino-hexopyranoside)

The reaction of methyl 4,6-O-isopropylidene-2,3-O-thiocarbonyl-α-D-mannoside with methyl iodide gives two major products, methyl 3,6-dideoxy-3,6-diiodo-2-O-(methylthio)carbonyl-α-D-altropyranoside and methyl 2,3-O-carbonyl-6-deoxy-6-iodo-α-D-mannopyranoside, both of which lack the 4,6-O-isopropylidene grouping but contain the 6-deoxy-6-iodo function, and another minor product.One of the major product, methyl 3,6-dideoxy-3,6-diiodo-2-O-(methylthio)carbonyl-α-D-altropyranoside, is convertedinto methyl α-tyveloside by sequential reduction and ester removal.The incorporation of iodine at C 6 is seemingly due to hydrogen iodide, and may be suppressed in the presence of N,N,N,N-trtramethylnaphthalene-1,8-diamine or propylene oxide, or by the use of 4,6-O-benzylidene-2,3-O-thiocarbonyl-α-D-mannoside as substrate.Methyl iodide/propylene oxide is apparently an efficient combination for thiocarbonate (C=S) into carbonate conversion.The structure of the minor product was shown by single-crystal X-ray diffraction to be 1,6-anhydro-3-deoxy-3-iodo-2-O-(methylthio)carbonyl-β-D-altropyranose.