65391-11-9

Basic information

• Product Name: (-)-Methyl-2,3-anhydro-4,6-O-benzyliden-α-D-gulopyranosid
• CAS NO: 65391-11-9
• Molecular Weight: 264.278
• Mol File: 65391-11-9.mol

Chemical Properties

• CAS DataBase Reference: (-)-Methyl-2,3-anhydro-4,6-O-benzyliden-α-D-gulopyranosid(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Methyl-2,3-anhydro-4,6-O-benzyliden-α-D-gulopyranosid(65391-11-9)
• EPA Substance Registry System: (-)-Methyl-2,3-anhydro-4,6-O-benzyliden-α-D-gulopyranosid(65391-11-9)

Safety Data

• Hazardous Substances Data: 65391-11-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 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] 
• 65530-21-4 methyl 4,6-O-benzylidene-2,3-di-O-methanesulfonyl-α-D-glucopyranoside 
• 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 
• 71-43-2 benzene 
• 28538-12-7 methyl-[O²-benzoyl-O⁴,O⁶-((S)-benzylidene)-O³-(toluene-4-sulfonyl)-α-D-galactopyranoside] 
• 6315-52-2 1,2-bis-tosyloxyethane 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 6748-92-1 methyl-[O³-benzoyl-O⁴,O⁶-((S)-benzylidene)-O²-(toluene-4-sulfonyl)-α-D-galactopyranoside] 
• 18031-56-6 methyl-[O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside] 
• 2872-56-2 methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 138638-64-9 Methyl 4,6-O-benzylidene-3-deoxy-3-phenylselenyl-α-D-altropyranoside 
• 84170-91-2 methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside 
• 193271-74-8 methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside 
• 193271-77-1 (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde 
• 144901-24-6 methyl 4,6-O-benzylidene-3-deoxy-3-N-dimethylamino-α-D-glucopyranoside N-oxide 
• 74410-50-7 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-2-ulose 
• 74430-69-6 methyl 3-O-benzyl-4,6-O-benylidene-2-(E)-hydroxyimino-α-D-ribo-hexopyranoside 
• 74430-68-5 methyl 3-O-benzyl-4,6-O-benylidene-2-(Z)-hydroxyimino-α-D-ribo-hexopyranoside 
• 10396-60-8 methyl 3-amino-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside 
• 478944-12-6 Benzoic acid (1R,2S,3R)-3-hydroxy-2-methyl-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester 
• 478944-09-1 Benzoic acid (1R,2S,3S)-3,4-dihydroxy-2-methyl-1-vinyl-butyl ester 
• 478944-11-5 Benzoic acid (R)-1-((R)-(S)-1-oxiranyl-ethyl)-allyl ester 
• 79386-70-2 Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

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.

Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes

We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1.