3150-15-0

Usage

Uses

Used in Pharmaceutical Development:
METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE is used as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs with diverse therapeutic applications.
Used in Natural Product Synthesis:
In the field of natural product synthesis, METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE is utilized as a starting material for creating complex natural compounds, leveraging its unique structural features.
Used in Flavor Production:
METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE is employed in the production of flavors, where its reactivity and structural properties are harnessed to create a wide range of flavor compounds for the food and beverage industry.
Used in Organic Synthesis:
As a versatile building block in organic synthesis, METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE is used for the creation of various chemical compounds with distinct biological and chemical properties, expanding the scope of chemical research and applications.

InChI:InChI=1/C14H16O5/c1-15-14-12-11(18-12)10-9(17-14)7-16-13(19-10)8-5-3-2-4-6-8/h2-6,9-14H,7H2,1H3/t9-,10-,11-,12-,13?,14+/m1/s1

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 
• 18031-56-6 methyl-[O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside] 
• 33535-04-5 methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 6748-92-1 methyl-[O³-benzoyl-O⁴,O⁶-((S)-benzylidene)-O²-(toluene-4-sulfonyl)-α-D-galactopyranoside] 
• 86420-67-9 methyl 4,6-O-benzylidene-α-D-galactopyranoside 2-O-p-toluenesulfonate 
• 86420-66-8 methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-di-O-p-toluenesulfonate 

Downstream Products

• 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 
• 117708-93-7 Methyl 2,3-anhydro-4,6-O-(phenylmethylene)-β-D-mannopyranoside 
• 15384-61-9 methyl 4,6-O-benzylidene-3-deoxy-3-N-dimethylamino-α-D-glucopyranoside 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 141115-75-5 methyl 2-O-benzyl-4,6-di-O-benzylidene-α-D-altropyranoside 
• 74410-51-8 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-altropyranoside 
• 134526-04-8 methyl 3-azido-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside 
• 84170-91-2 methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside 
• 137693-45-9 Me 3-O-ethyl-4,6-O-benzylidene-α-D-Alt 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

2-Diphenylarsino-, 2-diphenylphosphinyl-, and 2-triphenylstannyl-derivatives of methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranoside. Crystal structure of the phosphinyl derivative

Reaction of methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (3) with PhnMLi gives methyl 4,6-O-benzylidene-2-deoxy-2-M-α-D-altropyranoside (4; M=Ph2As, Ph2P or Ph3Sn).Compound (4, M=Ph2P) is readily oxidised in air to the phosphinyl derivative (4, M=Ph2P(O)).Characterisation of (4, M=Ph2As, Ph2P(O), or Ph3Sn) was achieved by NMR spectroscopy, including solid state NMR spectroscopy, for (4, M=Ph2As) and (4, M=Ph3Sn), and by X-ray crystallography for .In the solid state both the benzylidene and pyranose rings in , adopt chair conformations.The pentavalent phosphorus atom has a distorted tetrahedral geometry with C-P-C valency angles in the narrow range from 105.7(3) to 106.0(3) deg and the C-P-O valency angles ranging from 111.3(3) to 115.6(2) deg; the P-Caryl bond lengths are 1.808(5) and 1.815(6) Anagstroem, while the P-Calkyl bond length is slightly larger, being 1.829(6) Angstroem.Intermolecular H-bonding, involving HO and O(P) centres, links the molecules in the crystal.Keywords: Tin; Phosphorus; Arsinic; Pyranosides; Crystal structure

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.

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.

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.

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.

Base-promoted rearrangement of sugar epoxides to unsaturated sugars

(Chemical Equation Presented) A simple and efficient method for rearranging 2,3-anhydro carbohydrates to unsaturated sugars has been developed. The exceptionally mild reaction conditions and high stereoselectivity should make this an attractive method for the preparation of unsaturated carbohydrate derivatives.