40653-15-4

Upstream product

• 74247-81-7 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside 
• 20231-36-1 methyl 6-O-trityl-α-D-mannopyranoside 
• 2595-06-4 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran 
• 162147-37-7 C₃₇H₅₂O₆Si 
• 186540-03-4 tert-Butyl-diphenyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 791820-19-4 methyl 2,3,4-tri-O-benzyl-6-monomethoxytrityl-α-D-mannopyranoside 
• 191332-82-8 methyl 6-O-(4-methoxyphenyldiphenylmethyl)-α-D-mannopyranoside 

Downstream Products

• 155020-95-4 methyl (6R)-2,3,4-tri-O-benzyl-6-(2-thiazolyl)-β-D-galactopyranoside 
• 127588-70-9 (R)-2-(Isopropoxy-dimethyl-silanyl)-1-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethanol 
• 155020-83-0 methyl (6R)-2,3,4-tri-O-benzyl-6-(2-thiazolyl)-α-D-mannopyranoside 
• 155020-89-6 methyl (6S)-2,3,4-tri-O-benzyl-6-(2-thiazolyl)-α-D-glucopyranoside 
• 155020-87-4 methyl (6R)-2,3,4-tri-O-benzyl-6-(2-thiazolyl)-α-D-glucopyranoside 
• 154918-84-0 methyl 2,3,4-tri-O-benzyl-7-deoxy-L-glycero-α-D-manno-heptopyranoside 
• 154918-85-1 methyl 2,3,4-tri-O-benzyl-7-deoxy-D-glycero-α-D-manno-heptopyranoside 
• 122588-55-0 methyl-2,3,4-tri-O-benzyl-7-(Si-dimethylphenyl-silyl)-L-glycero-α-Dmanno-heptopyranoside 
• 113421-14-0 methyl (E)-2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-manno-oct-6-enodialdo-1,5-pyranoside 
• 125287-97-0 methyl uronate 
• 162284-46-0 methyl-2,3,4-tri-O-benzyl-7,8-dideoxyl-L-glycero-α-D-manno-oct-7-ynopyranoside 
• 211231-26-4 methyl 2,3,4,7-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside 
• 211231-29-7 methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside 
• 220853-26-9 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-diethoxyphosphinoylmethylene-α-D-mannopyranoside 

Relevant academic research and scientific papers

Rapid Entry into Biologically Relevant α,α-Difluoroalkylphosphonates Bearing Allyl Protection-Deblocking under Ru(II)/(IV)-Catalysis

A convenient synthetic route to α,α-difluoroalkylphosphonates is described. Structurally diverse aldehydes are condensed with LiF2CP(O)(OCH2CH-CH2)2. The resultant alcohols are captured as the pentafluorophenyl thionocarbonates and efficiently deoxygenated with HSnBu3, BEt3, and O2, and then smoothly deblocked with CpRu(IV)(π-allyl)quinoline-2-carboxylate (1-2 mol %) in methanol as an allyl cation scavenger. These mild deprotection conditions provide access to free α,α-difluoroalkylphosphonates in nearly quantitative yield. This methodology is used to rapidly construct new bis-α,α-difluoroalkyl phosphonate inhibitors of PTPIB (protein phosphotyrosine phosphatase-1B).

Synthesis and biological evaluation of two mannose 6-phosphate analogs

Two β-hydroxyphosphonate analogs of M6P have been prepared by condensation of the lithiated anion of methyldiethylphosphonate with the C-6 carbonyl of a mannose derivative. The diastereoisomers thus obtained have been separated and the absolute configurat

USE OF MANNOSE 6 PHOSPHATE AND MODIFICATIONS THEREOF FOR MEMORY ENHANCEMENT AND REDUCING MEMORY IMPAIRMENT

Provided are compositions and methods for memory enhancement, including recovery of memory impairment. The compositions and methods relate to mannose-6-phosphate and derivatives of mannose-6-phosphate. The methods relate to administration of M6P or derivatives thereof to individuals in whom memory enhancement is desired.

USE OF IGF-2 RECEPTOR AGONIST LIGANDS FOR TREATMENT OF ANGELMAN SYNDROME AND AUTISM

Provided are methods for treatment of neurodevelopmental disorders, such as Angelman Syndrome and autism comprising administering to an individual a composition comprising an agonist ligand of IGF -2 receptor. The agonist ligand of IGF-2 receptor may be IGF -2, or mannose-6-phosphate or a derivative thereof. Compositions comprising mannose-6-phosphate derivatives are also disclosed.

Synthesis of D-glycero-D-manno-heptose 1,7-bisphosphate (HBP) featuring a β-stereoselective bis-phosphorylation

D-glycero-D-manno-Heptose 1,7-bisphosphate (HBP) plays a unique role in bacteriology. We describe in this study a very efficient synthesis of HBP, featuring a highly 6-D-selective construction of the heptose scaffold as well as a double phosphorylation st

Multigram-scale synthesis of L,D-heptoside using a Fleming-Tamao oxidation promoted by mercuric trifluoroacetate

An efficient multigram-scale synthesis of methyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside from methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside is reported. It involves a sequence of Swern oxidation, Grignard addition and Fleming-Tamao reac

Synthesis of mannoheptose derivatives and their evaluation as inhibitors of the lectin LecB from the opportunistic pathogen Pseudomonas aeruginosa

Abstract Biofilm formation and chronic infections with Pseudomonas aeruginosa depend on lectins produced by the bacterium. The bacterial C-type lectin LecB binds to the two monosaccharides l-fucose and d-mannose and conjugates thereof. Previously, d-manno

General Homologation Strategy for Synthesis of l -glycero- and d -glycero-Heptopyranoses

A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed α-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

NOVEL MANNOPYRANOSIDE DERIVATIVES WITH ANTICANCER ACTIVITY

The present invention relates to mannopyranoside-derived compounds and to the use thereof as medicaments, in particular in the treatment of cancer diseases, and also to the method for preparing same and to pharmaceutical compositions comprising such compo

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