127214-37-3

Upstream product

• 83051-88-1 methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 19493-09-5 Methylenetriphenylphosphorane 
• 1031-15-8 methyltriphenylphosphonium chloride 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 79-37-8 oxalyl dichloride 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 210834-15-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 27200-84-6 methyl triphenylphosphonium bromide 

Downstream Products

• 103597-20-2 methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside 
• 103597-24-6 methyl 2,3,4-tri-O-benzyl-L-glycero-α-D-gluco-heptopyranoside 
• 133918-92-0 METHYL 2,3,4-TRI-O-BENZYL-6-DEOXY-α-D-GLUCOHEPTOPYRANOSIDE 
• 306299-94-5 1-O-acetyl-2,3,4-tri-O-benzyl-6,7-dideoxy-D-gluco-hept-6-enopyranose 
• 294209-73-7 2,3,4-tri-O-benzyl-6,7-dideoxy-D-gluco-hept-6-eno-1,5-lactone 
• 294209-74-8 2,6-abhydro-3,4,5-tri-O-benzyl-1,7,8-trideoxy-D-gluco-octa-1,7-dienitol 

Relevant academic research and scientific papers

Study on metal-induced reactions of α-diazocarbonyl glucosides

Conversions of diazocarbonyl carbohydrate compounds catalyzed by a series of rhodium and copper catalysts in conventional heating or microwave conditions were investigated. C-H insertion product was obtained in the presence of Rh 2(OAc)4. Intermolecular reactions rather than intramolecular reactions occurred in the presence of copper catalysts.

Systematic synthesis of inhibitors of the two first enzymes of the bacterial heptose biosynthetic pathway: Towards antivirulence molecules targeting lipopolysaccharide biosynthesis

L-Heptoses (L-glycero-D-manno-heptopyranoses) are constituents of the inner core of lipolysaccharide (LPS), a molecule playing key roles in the mortality of many infectious diseases as well as in the virulence of many human pathogens. The inhibition of the first enzymes of the bacterial heptose biosynthetic pathway is an almost unexplored field to date although it appears to be a very novel way for the development of antivirulence drugs. We report the synthesis of a series of D-glycero-D-manno-heptopyranose 7-phosphate (H7P) analogues and their inhibition properties against the isomerase GmhA and the the kinase HldE, the two first enzymes of the bacterial heptose biosynthetic pathway. The heptose structures have been modified at the 1-, 2-, 6- and 7-positions to probe the importance of the key structural features of H7P that allow a tight binding to the target enzymes; H7P being the product of GmhA and the substrate of HldE, the second objective was to find structures that could simultaneously inhibit both enzymes. We found that GmhA and HldE were extremely sensitive to structural modifications at the 6- and 7- positions of the heptose scaffold. To our surprise, the epimeric analogue of H7P displaying a D-glucopyranose configuration was found to be the best inhibitor of both enzymes but also the only molecule of this series that could inhibit GmhA (IC50=34 μM) and HldE (IC50=9.4 μM) in the low micromolar range. Noteworthy, this study describes the first inhibitors of GmhA ever reported, and paves the way to the design of a second generation of molecules targeting the bacterial virulence. Copyright

Synthesis of (6,6′)-C-linked pseudodisaccharides

A series of (6,6′)-C-linked pseudodisaccharides has been prepared using a general synthetic strategy of olefin metathesis in the presence of Grubbs second-generation catalyst. Yields were excellent in every case.

Stereoselective glycal fluorophosphorylation: Synthesis of ADP-2-fluoroheptose, an inhibitor of the LPS Biosynthesis

Heptosides are found in important bacterial glycolipids such as lipopolysaccharide (LPS), the biosynthesis of which is targeted for the development of novel antibacterial agents. This work describes the synthesis of a fluorinated analogue of ADP-L-glycero-β-D-manno-heptopyranose, the donor substrate of the heptosyl transferase WaaC, which catalyzes the incorporation of this carbohydrate into LPS. Synthetically, the key step for the preparation of ADP-2F-heptose is the simultaneous and stereoselective installation of both the fluorine atom at C-2 and the phosphoryl group at C-1 through a selectfluor-mediated (selectfluor= 1-chloromethyl-4-fluorodiazoniabicyclo[2.2.2] octane bis(triflate)) electrophilic addition/nucleophilic substitution involving a heptosylglycal. Therefore, we detail in this article 1) the stereoselective preparation of the key intermediates heptosylglycals, 2) the development of a new fluorophosphorylation procedure allowing an excellent β-gluco stereoselectivity with "all-equatorial" glycals, 3) the synthesis of the target ADP-2F-heptose, and 4) some comments on the contacts observed between the fluorine atom of the final molecule and the protein in the crystallographic structure of heptosyltransferase WaaC.

Synthesis of vinyl- and alkynylcyclopentanetetraols by SmI2/Pd(0)-promoted carbohydrate ring-contraction

A variety of vinyl- or alkynyl-substituted polyhydroxylated cyclopentanes and cyclobutanes are prepared in enantiomerically pure form from appropriate carbohydrate precursors, in a direct one-step ring-contraction procedure promoted by SmI2 and catalytic Pd(0). This reaction is thought to proceed through intermediate ring-opened allyl- or allenylsamarium complexes that undergo ring-closure by intramolecular carbonyl addition. A predominant trans relationship is found between vinyl (or alkynyl) and hydroxyl groups at the two newly created stereogenic centers, with good to excellent levels of stereoselectivity being observed in the formation of homopropargyl cyclopentanol products. Under appropriate conditions, preparatively useful yields are realized of stereoisomers not directly available using alternative methodology.

Synthesis of glycosyl chlorides with acid-labile protecting groups

Glycosyl chlorides with acid-labile protecting groups were prepared from their corresponding alcohols under basic conditions in good yields. The synthesis of a 1,6-C-linked disaccharide was carried out via reaction of a glycosyl chloride with an aldehyde

Samariumdiiodid-vermittelte Kupplung von Glycosylphosphaten mit Kohlenstoffradikal- oder -anion-Acceptoren - Synthese von C-Glycosiden

Keywords: C-Glycoside; Verknuepfungen; Samariumverbindungen; Synthesemethoden

Preparation of sugar-derived α-acetoxy-aldehydes

A convenient method for conversion of sugar diols (2a-2d) into a-acetoxy-aldehydes: 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranos-6-ulose (5a), 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranos-6-ulose (5b), methyl 6-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco- and L-glycero-α-D-gluco-heptopyranosid-7-uloses (5c and 5d respectively) is presented. This involves the protection (as TBDMS ether) of the primary hydroxyl group, acetylation of the remaining secondary one and desilylation followed by a Swern oxidation. Partial migration of the acetyl group during desilylation (with Bu4NF) was observed for compound 4a and complete migration for 4f. α-Acetoxy-aldehydes 5a-5d were characterized as adducts with Ph3P = CH-CO2Me (12a-12d).

α-glucosidase inhibitors

This invention relates to novel polyglycosidyl derivatives of 1-deoxy-nojirimycin, to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes.