14133-63-2

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2,3-O-ISOPROPYLIDENE-ALPHA-L-RHAMNOPYRANOSE is used as a building block for the synthesis of various pharmaceuticals and bioactive compounds. Its unique structure and reactivity make it valuable for the formation of complex molecules in drug discovery.
Used in Organic Synthesis:
METHYL 2,3-O-ISOPROPYLIDENE-ALPHA-L-RHAMNOPYRANOSE is used as a building block in organic synthesis for the creation of complex molecules. Its unique structure and reactivity make it valuable in chemical research.
Used in Carbohydrate Chemistry:
METHYL 2,3-O-ISOPROPYLIDENE-ALPHA-L-RHAMNOPYRANOSE is used as a building block in carbohydrate chemistry for the synthesis of various natural products and sugar derivatives. Its ability to protect the hydroxyl group of the sugar molecule makes it particularly useful in the formation of glycosidic linkages.

Upstream product

• 72959-83-2 methyl-[O²,O³-isopropylidene-O⁴-(toluene-4-sulfonyl)-α-L-rhamnopyranoside] 
• 67-56-1 methanol 
• 3615-41-6 L-Rhamnose 
• 67-64-1 acetone 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 76178-07-9 methyl 2,3-O-isopropylidene-4-O-(methylthio)thiocarbonyl-α-L-rhamnopyranoside 
• 75754-53-9 2-Oxo-propionic acid (3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 77-76-9 2,2-dimethoxy-propane 
• 6014-42-2 L-rhamnose 
• 1128-40-1 methyl L-rhamnopyranoside 
• 15814-59-2 (2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 22932-34-9 methyl 6-deoxy-6-iodo-2,3-O-isopropylidene-α-D-mannopyranoside 
• 112612-45-0 methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 85726-76-7 methyl 4-O-benzoyl-2,3-O-isopropylidene-α-D-rhamnopyranoside 

Downstream Products

• 52681-72-8 methyl-4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 126330-72-1 (3aR,4R,6S,7S,7aR)-4-Methoxy-2,2,6-trimethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 126330-72-1 (3aR,4R,6S,7S,7aR)-4-Methoxy-2,2,6-trimethyl-7-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 71080-20-1 methyl 2,3-O-isopropylidene-4-O-trityl-α-L-rhamnopyranoside 
• 35775-14-5 methyl 4-O-benzyl-6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside 
• 25019-68-5 methyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 25019-69-6 methyl 4-O-benzyl-α-L-rhamnopyranoside 
• 126330-72-1 (3aR,4R,6S,7S,7aR)-4-Methoxy-2,2,6-trimethyl-7-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 126330-66-3 methyl 4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 34819-86-8 3,4-di-O-acetyl-6-deoxy-L-glucal 
• 76209-09-1 methyl 4-O-(4-O-benzoyl-2,3-O-cyclohexylidene-β-L-rhamnopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 84094-48-4 methyl 4-O-(diphenylphosphino)-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 110224-84-5 Acetic acid (2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-4-yl ester 
• 111373-93-4 methyl 2,3-O-isopropylidene-4-O-(p-bromobenzyl)-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Improved Synthesis for Modular Ascarosides Uncovers Biological Activity

A versatile synthesis of modular ascarosides, a family of signaling molecules from Caenorhabditis elegans and other nematodes, via hydrogenolysis of a cyclic sulfate derived from methyl-α-l-rhamnopyranoside is reported. The route enables selective introdu

USE OF FUCOSYLATION INHIBITOR FOR PRODUCING AFUCOSYLATED ANTIBODY

The present invention provides inhibitors of fucosylation during protein expression from mammalian cells. The inhibitors are derived from rhamnose and act by inhibition of GDP-mannose 4,6-dehydratase (GMD). The invention further provides methods of making

BIARYL AMIDES WITH MODIFIED SUGAR GROUPS FOR TREATMENT OF DISEASES ASSOCIATED WITH HEAT SHOCK PROTEIN PATHWAY

Provided are biaryl amides and coumarin-based compounds with modified sugar groups for treatment of diseases associated with heat shock protein pathway. The compounds having the following formulas, wherein variables are as defined herein. Formulae (I), (II), (III), (IV), and (V), Pharmaceutical compositions of the compounds are also provided. These biaryl amides and coumarin-based derivatives with modified sugar groups are useful for treatment and prevention of diseases and disorders, including neurological disorders, such as neurodegenerative diseases and nerve damaging disorders, for example, diabetic peripheral neuropathy.

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables a novel Barton–McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.

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.

Mechanistic investigation of the radical S -adenosyl- L -methionine enzyme DesII using fluorinated analogues

DesII is a radical S-adenosyl-l-methionine (SAM) enzyme that can act as a deaminase or a dehydrogenase depending on the nature of its TDP-sugar substrate. Previous work has implicated a substrate-derived, C3-centered α-hydroxyalkyl radical as a key interm

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.

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.

Synthesis of disaccharides containing 6-Deoxy-α-L-talose as potential heparan sulfate mimetics

A 6-deoxy-α-L-talopyranoside acceptor was readily prepared from methyl α-L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired α-linked disaccharide (69-90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (α:β = 6:1), but the desired α-linked disaccharide could be isolated in good overall yield (60%) following conversion into its corresponding tribenzoate derivative. The disaccharides were designed to mimic the heparan sulfate (HS) disaccharide GlcN(2S,6S)-IdoA(2S). However, the intermediates readily derived from these disaccharides were not stable to the sulfonation/deacylation conditions required for their conversion into the target HS mimetics.

Easy access to L -mannosides and L -galactosides by using cih activation of the corresponding 6-deoxysugars

Rare sugars by CH activation: The title compounds have been prepared from the corresponding 6-deoxysugars by an intramolecular CiH activation in high yields. Diethyl silane is attached to the 4-OH group followed by formation of a SiiC bond; both transformations are catalyzed by iridium in a one-pot fashion. The subsequent Fleming-Tamao oxidation provided the L-sugars. Copyright