70774-92-4

Upstream product

• 2232-08-8 N-tosylimidazole 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 50-99-7 D-glucose 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 4124-41-8 p-toluenesulfonylanhydride 
• 120200-47-7 methyl-[O³-benzoyl-O⁴,O⁶-((R)-benzylidene)-O²-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 109-86-4 2-methoxy-ethanol 
• 127-09-3 sodium acetate 

Downstream Products

• 79297-68-0 methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside 
• 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 
• 134526-04-8 methyl 3-azido-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside 
• 160636-37-3 methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 162678-87-7 Methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 175978-55-9 methyl 2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 501088-17-1 methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 160301-08-6 3-Iodomethyl-isochroman-1-one 
• 189144-35-2 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-toluenesulfonyl)-α-D-glucopyranoside 
• 93302-38-6 (2R,4aR,6S,7R,8R,8aR)-6,8-dimethoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol 
• 748154-83-8 (diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester 
• 748154-82-7 Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester 

Relevant academic research and scientific papers

Highly Efficient Selective Benzylation of Carbohydrates Catalyzed by Iron(III) with Silver Oxide and Bromide Anion as Co-catalysts

A highly efficient, green, and regioselective method for the benzylation of diols and polyols was developed. With the use of Ag2O (0.6 equiv.) and tetrabutylammonium bromide (0.1 equiv.) as co-catalysts, the iron(III)-catalyzed benzylation reaction proceeded to completion at 40 °C within 2–3 h and gave the products in high yields with high regioselectivities. A mechanism involving the principle of enhanced basicity of Ag2O by soft anions was proposed.

Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids

Direct oxidation of the 4,6-O-benzylidene acetal protecting group to C-6 carboxylic acid has been developed that provides an easy access to a wide range of biologically important and synthetically challenging uronic acid and sugar amino acid derivatives in good yields. The RuCl3-NaIO4-mediated oxidative cleavage method eliminates protection and deprotection steps and the reaction takes place under mild conditions. The dual role of the benzylidene acetal, as a protecting group and source of carboxylic acid, was exploited in the efficient synthesis of six-carbon sialic acid analogues and disaccharides bearing uronic acids, including glycosaminoglycan analogues.

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 convenient synthesis of orthogonally protected 2-deoxystreptamine (2-DOS) as an aminocyclitol scaffold for the development of novel aminoglycoside antibiotic derivatives against bacterial resistance

The development of new aminoglycoside analogues to reduce the emergence of bacterial resistance has become a topic of high interest. We describe here a rapid and facile access to orthogonally protected 2-deoxystreptamine (2-DOS), a meso-diaminocyclitol known to be a pivotal component of most active aminoglycosides. Our synthetic approach started from highly protected methyl α-d-glucopyranoside which in turn was converted by a Ferrier rearrangement into an enantiopure polyfunctionalized cyclohexane ring. Finally, two different N-protected groups were successively introduced. The first one was inserted as an oximino benzylether followed by a diastereofacial hydride reduction, working with Me4NBH(OAc)3 only in TFA at low temperature rather than in AcOH as usual. The second group was introduced by displacement of a hydroxyl group through a Mitsunobu reaction using a DPPA-DIAD-Ph3P system for azide transfer. The Royal Society of Chemistry.

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.

On the selectivity of stannylene-mediated alkylation and esterification of methyl 4,6-O-benzylidene α-D-glucopyranoside

Keywords: Methyl 4,6-O-benzylidene-α-D-glucopyranoside; Regiospecificity; Alkylation; Esterification; Stannylene

Regioselective monotosylation of non-protected and partially protected glycosides by the dibutyltin oxide method

Tosylation of non-protected glycopyranosides with p-toluenesulfonyl chloride in the presence of 4-dimethylaminopyridine, after activiation of the glycosides by dibutyltin oxide, gave mono-O-tosylates in good yield. The regioselectivity in this tosylation