3150-16-1

Usage

Uses

Used in Carbohydrate Chemistry:
Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside is used as a key intermediate in carbohydrate chemistry for the synthesis of complex carbohydrates. Its unique structure allows for the formation of various glycosidic linkages, making it a valuable component in the development of novel carbohydrate-based compounds.
Used in Pharmaceutical Development:
Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside is used as a building block in the development of novel pharmaceuticals. Its potential applications in glycosylation reactions and the synthesis of complex carbohydrates make it a promising candidate for the creation of new drug molecules with improved therapeutic properties.
Used in Study of Carbohydrate-Protein Interactions:
Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside is used as a research tool for studying carbohydrate-protein interactions. Its unique structure allows for the investigation of how carbohydrates interact with proteins, which can provide insights into the development of carbohydrate-based materials for various technical applications.
Used in Design of Carbohydrate-Based Materials:
Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside is used as a component in the design of carbohydrate-based materials for various technical applications. Its properties and unique structure make it a valuable building block for the development of new materials with specific properties and functions.

Upstream product

• 120200-47-7 methyl-[O³-benzoyl-O⁴,O⁶-((R)-benzylidene)-O²-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 99265-93-7 methyl-[O⁴,O⁶-((R)-benzylidene)-O²,O³-bis-(toluene-4-sulfonyl)-α-D-altropyranoside] 
• 3053-12-1 methyl-[O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O²-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 70774-92-4 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside 
• 28538-15-0 methyl-[O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-O³-methanesulfonyl-α-D-altropyranoside] 
• 127-09-3 sodium acetate 
• 129217-24-9 4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside 
• 144828-39-7 (2R,4aR,6S,7S,8S,8aS)-8-(3,4-Diphenyl-pyrrolidin-1-yl)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 71117-41-4 methyl 4,6-O-benzylidene-α-D-altropyranoside 
• 65530-21-4 methyl 4,6-O-benzylidene-2,3-di-O-methanesulfonyl-α-D-glucopyranoside 
• 50-99-7 D-glucose 

Downstream Products

• 497180-22-0 methyl-[O⁴,O⁶-((R)-benzylidene)-3-iodo-3-deoxy-α-D-altropyranoside] 
• 626200-80-4 methyl 4,6-O-benzylidene-3-deoxy-3-C-ethyl-α-D-altropyranoside 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 
• 71184-15-1 methyl-3-deoxyamino-4,6-dioxabenzylidene-α-D-altropyranose 
• 6198-74-9 methyl (R)-3-deoxy-α-D-arabinohexopyranose 
• 72904-78-0 methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside 
• 71117-41-4 methyl 4,6-O-benzylidene-α-D-altropyranoside 
• 30571-48-3 methyl-[O⁴,O⁶-((R)-benzylidene)-3-bromo-3-deoxy-α-D-altropyranoside] 
• 74410-53-0 Methyl 4,6-O-benzylidene-3-O-methyl-α-D-altropyranoside 
• 131529-46-9 methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-methylprop-2-enyl)-α-D-altroside 
• 131613-80-4 methyl 4,6-O-benzylidene-3-chloro-3-deoxy-α-D-altroside 
• 131529-45-8 methyl 4,6-O-benzylidene-3-deoxy-3-(prop-2-enyl)-α-D-altropyranoside 
• 138638-68-3 Methyl 4,6-O-benzylidene-2-deoxy-2-phenylselenyl-α-D-glucopyranoside 
• 138638-64-9 Methyl 4,6-O-benzylidene-3-deoxy-3-phenylselenyl-α-D-altropyranoside 

Relevant academic research and scientific papers

A Domino Epoxide Ring-Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars

A sterereospecific and efficient synthesis of thiosugars derived from levoglucosenone and methyl α-d-glucopyranoside was developed by a domino epoxide ring opening- xanthate migration to afford 1,3-oxathiolane-2-thiones in high yields. The stereochemical outcome of the new C–S bond was defined by the configuration of the starting materials. The 1,3-oxathiolane-2-thiones were subsequently submitted to a second tandem reaction affording the corresponding 2,3-episulfide alcohols. The thiosugars obtained are useful building blocks for the synthesis of thiooligosaccharides with potential biological properties.

Diaminohexopyranosides as ligands in half-sandwich ruthenium(II), rhodium(III), and iridium(III) complexes

The syntheses of methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-d-hexopyranosides of glucose, mannose, gulose, and talose and methyl 2-amino-4,6-benzylidene-2,3-dideoxy-3-tosylamido-α-d-glucopyranoside are exhaustively presented, as well as their application as ligands in half-sandwich ruthenium(II), rhodium(III), and iridium(III) complexes. The complex formation occurs highly diastereoselectively, creating a stereogenic metal center. The molecular structures of the ligands and their complexes were investigated by X-ray structure analysis, NMR spectroscopy, polarimetry, and DFT methods. The diamino monosaccharide complexes have been subjected to antitumor activity studies. In vitro tests of a few ruthenium complexes against different cancer cell types showed antiproliferative activities 4-10 times lower than that of cisplatin.

SUGAR-LINKER-DRUG CONJUGATES

The present disclosure relates to sugar-linker-drug conjugates, of the formula [A-B-]n-L-D, wherein A is a saccharide; B is a spacer, n is an integer selected from 1 to 3; L is a linker group and D is a drug having a chemically reactive functional group selected from the group consisting of a primary or secondary amine, hydroxyl, sulfhydryl, carboxyl, aldehyde and ketone. Pharmaceutical compositions comprising the conjugates and methods of using thern are also provided.

SACCHARIDE CONJUGATES

This invention relates to compounds comprising a saccharide conjugated to an imaging agent or a reporter group, compositions comprising them and methods of using them. Specifically BLM-disaccharide and BLM-monosaccharide conjugates containing different linker groups and an imaging agent or a reporter group are provided for the targeting and imaging of tumors.

AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM

The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.

Synthesis of ribo-hexopyranoside- and altrose-based azacrown ethers and their application in an asymmetric Michael addition

The synthesis of four new ribo-hexopyranoside-based chiral lariat ethers of monoaza-15-crown-5 type and two altropyranoside-based crown ethers were elaborated. Our syntheses utilized the regioselective ring opening of the oxiran moiety of the 2,3-anhydro sugars by nucleophilic reagents to afford the key intermediates. The reaction of methyl-2,3-anhydro-4,6-O-benzylidene-α-d- mannopyranoside with ethanolamine is especially of interest to afford a 3-substituted altropyranoside. One of the ribo-hexopyranoside-based lariat ethers with a 4-methoxyphenyl substituent induced an enantioselectivity of 80% when used as catalyst in the Michael addition of diethyl acetamidomalonate to trans-β-nitrostyrene under phase transfer catalytic conditions.

A scalable approach to obtaining orthogonally protected β-d-idopyranosides

A practical method to obtain orthogonally protected d-idopyranose from d-galactose has been developed, which is the first method to enable synthesis of the challenging β-d-idopyranoside linkage. The method relies on a key double inversion at O-2 and O-3 in an easily prepared d-galactose derivative, which proceeds regio- and stereoselectively through a 2,3-anhydrotalopyranoside; reaction using a selection of alkoxides affords exclusively the 3-O-alkylidopyranoside, which can be used to generate an orthogonally protected monosaccharide. The process is scalable and requires minimal purification, so it could be used to produce building blocks to aid in the synthesis of various β-idopyranose-containing oligosaccharide targets to further probe their biological functions.

Synthesis of 3-amido-3-deoxy-β-d-talopyranosides: All-cis-substituted pyranosides as lectin inhibitors

3-Deoxy-3-amino-β-d-talopyranosides have been synthesized for the first time. The amines were obtained from galactopyranosides through 2,3-anhydrogulosides that were opened to idosides followed by an oxidation/reductive amination sequence. From the amines, 11 corresponding 3-deoxy-3-arylamido-β-talopyranosides have been synthesized and evaluated as inhibitors against galectin-1, -2, -3, -4C, -4N, -7, -8N and -9N. The synthesized talosamides showed selectivity for Galectin-4C with three of the monosaccharides having dissociation constants at around 100 μM against the lectin, which is more than two orders of magnitude better than methyl β-galactoside and significantly better than the previous best galectin-4C monosaccharide inhibitor.

Synthesis of guanidines from azides: A general and straightforward methodology in carbohydrate chemistry

(Figure presented) The ability of the guanidinylating reagent N′,N′′-diBoc-N-triflyl-guanidine (GN-Tf) to react with in situ formed free amines from azides in carbohydrate scaffolds was explored. This reaction proved to be an efficient method to prepare guanidine derivatives in a one-pot manner with good to excellent yields, either with primary or secondary azides with different substitution patterns. Labile protecting groups such as benzyl ethers are not removed under these hydrogenolytic conditions.

Assignment of the absolute configuration of blasticidin A and revision of that of aflastatin A

The absolute configuration of blasticidin A, a strong inhibitor of aflatoxin production by Aspergillus parasiticus, was assigned by adding the data of relative configurations at its diol and pentaol moieties to previously known stereochemistry. Similarity