22932-38-3

Basic information

• Product Name: methyl 6-deoxy-2,3-O-isopropylidene-α-D-glucopyranoside
• CAS NO: 22932-38-3
• Molecular Weight: 218.25
• Mol File: 22932-38-3.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: methyl 6-deoxy-2,3-O-isopropylidene-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-deoxy-2,3-O-isopropylidene-α-D-glucopyranoside(22932-38-3)
• EPA Substance Registry System: methyl 6-deoxy-2,3-O-isopropylidene-α-D-glucopyranoside(22932-38-3)

Safety Data

• Hazardous Substances Data: 22932-38-3(Hazardous Substances Data)

Upstream product

• 67-64-1 acetone 
• 15814-59-2 (2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 77-76-9 2,2-dimethoxy-propane 
• 145260-87-3 Benzoic acid (3aR,4S,6R,7R,7aS)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 116-11-0 2-Methoxypropene 
• 5155-43-1 methyl 6-deoxy-α-D-glucopyranoside 
• 10368-81-7 methyl 4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside 
• 14133-63-2 methyl 6-deoxy-2,3-O-isopropylidene-α-D-glucopyranoside 
• 42214-01-7 methyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 42214-02-8 methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose 
• 530-26-7 D-Mannose 
• 13035-60-4 methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside 
• 63167-69-1 methyl 2,3-O-isopropylidene-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 14133-63-2 methyl 6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside 
• 145260-85-1 C₄₉H₄₇NO₁₅ 
• 145260-84-0 C₄₄H₄₃NO₁₄ 
• 145260-75-9 C₄₄H₄₅NO₁₄ 
• 2592-54-3 methyl 2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranoside 
• 108319-55-7 benzyl 4-O-benzoyl-3-O-(4-O-benzoyl-2-bromo-2,6-dideoxy-3-O-formyl-β-D-glucopyranosyl)-2-bromo-2,6-dideoxy-β-D-galactopyranoside 
• 108319-54-6 benzyl 4-O-benzoyl-3-O-(4-O-benzoyl-2-bromo-2,6-dideoxy-3-O-formyl-α-D-glucopyranosyl)-2-bromo-2,6-dideoxy-β-D-galactopyranoside 
• 108319-53-5 benzyl 4-O-benzoyl-2-bromo-2,6-dideoxy-β-D-galactopyranoside 
• 108319-52-4 benzyl 4-O-benzoyl-2-bromo-2,6-dideoxy-3-O-formyl-β-D-galactopyranoside 
• 113879-98-4 Benzyl-O-(4-O-benzoyl-2-brom-2,6-didesoxy-β-D-glucopyranosyl)-(1->3)-O-(4-O-benzoyl-2-brom-2,6-didesoxy-β-D-glucopyranosyl)-(1->3)-4-O-benzoyl-2-brom-2,6-didesoxy-β-D-glucopyranosid 
• 108365-30-6 Benzyl-O-(4-O-benzoyl-2-brom-2,6-didesoxy-3-O-formyl-β-D-glucopyranosyl)-(1->3)-O-(4-O-benzoyl-2-brom-2,6-didesoxy-β-D-glucopyranosyl)-(1->3)-4-O-benzoyl-2-brom-2,6-didesoxy-β-D-glucopyranosid 
• 108319-56-8 benzyl 4-O-benzoyl-3-O-(2,6-dideoxy-3-O-formyl-β-D-arabino-hexopyranosyl)-2,6-dideoxy-β-D-lyxo-hexopyranoside 

Relevant articles and documents

Molecular recognition of brucella A and M antigens dissected by synthetic oligosaccharide glycoconjugates leads to a disaccharide diagnostic for brucellosis

The cell wall O-polysaccharides of pathogenic Brucella species are homopolymers of the rare sugar 4,6-dideoxy-4-formamido- α-d-mannopyranose. Despite the apparent simplicity of the polysaccharide it appears to be a "block copolymer" composed of A and M polysaccharide sequences expressed as a single molecule. The simultaneous presence of both in the cell wall has complicated the understanding of the molecular recognition of these antigens by antibodies present in the serum of infected animals and humans and by monoclonal antibodies. Since presumptive diagnosis of brucellosis, a serious disease in domestic livestock, wild animals, and humans, is based on detection of these antibodies it is important to separate the two antigenic epitopes, one of which is also found in other bacteria. Chemical synthesis provides the only means to achieve this outcome. A series of six oligosaccharides from di to hexasaccharides 1-6 were synthesized and conjugated to proteins to provide glycoconjugate antigens and conjugate vaccines. These chemically defined antigens identified the M antigenic determinant and provided a structural basis for understanding the fine specificity of monoclonal and polyclonal antibodies that bind the M antigen. This resulted in the discovery of a disaccharide that shows considerable potential as an unambiguous diagnostic antigen for detecting brucellosis in humans and animals and two hexasaccharide conjugate vaccine candidates that produce high levels of O-polysaccharide specific antibodies in mice.

Synthetic glycoconjugates characterize the fine specificity of: Brucella A and M monoclonal antibodies

The dominant cell wall antigen of Brucella bacteria is the O-polysaccharide component of the smooth lipopolysaccharide. Infection by various Brucella biovars causes abortions and infertility in a wide range of domestic and wild animals and debilitating disease in humans. Diagnosis relies on the detection of antibodies to the A and M antigens expressed in the O-polysaccharide. This molecule is a homopolymer of the rare monosaccharide, 4-formamido-4,6-dideoxy-d-mannopyranose (Rha4NFo). The A epitope is created by a uniform α1,2 linked internal polymeric sequence capped by a distinct tetrasaccharide sequence defining the M antigen. Unique oligosaccharides only available by chemical synthesis and conjugated via reducing and non-reducing residues to bovine serum albumin have revealed the structural basis of the fine specificity that allows the discrimination of these closely related A and M epitopes. All three M specific monoclonal antibodies (mAbs) are inferred to possess groove type binding sites open at each end, and recognize an α1,3 linked Rha4NFo disaccharide as a part of a trisaccharide epitope, which in two mAbs includes the terminal Rha4NFo residue. The binding site of one of these antibodies is sufficiently large to engage up to six Rha4NFo residues and involves weak recognition of α1,2 linked Rha4NFo residues. The third mAb binds an internal trisaccharide epitope of the M tetrasaccharide. Two A specific mAbs also possess groove type binding sites that accommodate six and four α1,2 linked Rha4NFo residues.

Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization

We report a bio-inspired, strain driven epimerization of trans-ketals to cis-ketals through an enolate intermediate. Swern oxidation of a hydroxyl group adjacent to a trans-ketal effects both oxidation and its epimerization to cis-ketal. This novel and general strategy allows inversion of up to three contiguous stereocenters and has been illustrated by the synthesis of several unnatural/rare isomers of carbohydrates/cyclitols from their naturally abundant isomers. This journal is the Partner Organisations 2014.