94118-99-7

Upstream product

• 16713-80-7 Acetic acid (3aR,5S,6R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 100-51-6 benzyl alcohol 
• 77988-67-1 Acetic acid (R)-2-acetoxy-1-((3aS,4R,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester 
• 100-44-7 benzyl chloride 
• 272780-73-1 C₁₉H₂₆O₆ 
• 74912-02-0 1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose 
• 94152-34-8 5,6-di-O-acetyl-1-O-benzyl-2,3-O-isopropylidene-β-L-gulofuranose 
• 3458-28-4 D-Mannose 
• 530-26-7 D-Mannose 
• 78039-06-2 phenylmethyl-2,3-O-(1-methylethylidene)-5,6-O-(N,N-dimethylaminomethylene)-α-D-mannofuranoside 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 100-39-0 benzyl bromide 
• 28978-37-2 1-O-benzyl-2,3-O-isopropylidene-5,6-di-O-mesyl-α-D-mannofuranose 

Downstream Products

• 102919-04-0 benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside 
• 96150-84-4 (3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 
• 78039-06-2 phenylmethyl-2,3-O-(1-methylethylidene)-5,6-O-(N,N-dimethylaminomethylene)-α-D-mannofuranoside 
• 96150-86-6 benzyl 2,3-O-(1-methylethylidene)-α-D-lyxofuranosiduronic acid chloride 
• 158780-49-5 (3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid allyl ester 
• 91364-12-4 benzyl 2,3-O-isopropylidene-6-O-trityl-α-D-lyxo-hexofuranosid-5-ulose 
• 91364-13-5 (3aS,4S,6R,6aS)-4-Benzyloxy-2,2-dimethyl-6-((R)-1-methylsulfanylmethoxy-2-trityloxy-ethyl)-tetrahydro-furo[3,4-d][1,3]dioxole 
• 14199-63-4 1-deoxymannojirimycin 
• 94119-04-7 benzyl 5-azido-5-deoxy-α-D-mannofuranoside 
• 94119-03-6 5-azido-1-O-benzyl-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranose 
• 94152-34-8 5,6-di-O-acetyl-1-O-benzyl-2,3-O-isopropylidene-β-L-gulofuranose 
• 94119-00-3 (S)-1-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethanol 
• 94119-02-5 [(R)-2-Azido-2-((3aS,4R,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethoxy]-tert-butyl-diphenyl-silane 
• 94119-01-4 Trifluoro-methanesulfonic acid (S)-1-((3aS,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl ester 

Relevant academic research and scientific papers

Third-Generation Amino Acid Furanoside-Based Ligands from d-Mannose for the Asymmetric Transfer Hydrogenation of Ketones: Catalysts with an Exceptionally Wide Substrate Scope

A modular ligand library of α-amino acid hydroxyamides and thioamides was prepared from 10 different N-tert-butyloxycarbonyl-protected α-amino acids and three different amino alcohols derived from 2,3-O-isopropylidene-α-d-mannofuranoside. The ligand library was evaluated in the half-sandwich ruthenium- and rhodium-catalyzed asymmetric transfer hydrogenation of a wide array of ketone substrates, including simple as well as sterically demanding aryl alkyl ketones, aryl fluoroalkyl ketones, heteroaromatic alkyl ketones, aliphatic, conjugated and propargylic ketones. Under the optimized reaction conditions, secondary alcohols were obtained in high yields and in enantioselectivities up to >99%. The choice of ligand/catalyst allowed for the generation of both enantiomers of the secondary alcohols, where the ruthenium-hydroxyamide and the rhodium-thioamide catalysts act complementarily towards each other. The catalytic systems were also evaluated in the tandem isomerization/asymmetric transfer hydrogenation of racemic allylic alcohols to yield enantiomerically enriched saturated secondary alcohols in up to 98% ee. Furthermore, the catalytic tandem α-alkylation/asymmetric transfer hydrogenation of acetophenones and 3-acetylpyridine with primary alcohols as alkylating and reducing agents was studied. Secondary alcohols containing an elongated alkyl chain were obtained in up to 92% ee. (Figure presented.).

Ultrasound-assisted selective deprotection of terminal acetonides catalyzed by silica-supported boron trifluoride

An efficient and convenient method for the selective cleavage of terminal acetonides is described. Treatment of terminal acetonides in the presence of a wide range of functional groups with silica-supported boron trifluoride as a catalyst furnished the corresponding diols in 82-95% yield under ultrasound irradiation conditions. The acid-labile p-methoxybenzyl group as a protecting group remained intact under the conditions employed to the present deprotection condition. Copyright Taylor & Francis Group, LLC.

Design, synthesis and pharmacological evaluation of omeprazole-like agents with anti-inflammatory activity

A new series of novel benzimidazole derivatives containing substituted pyrid-2-yl moiety and polyhydroxy sugar conjugated to the N-benzimidazole moiety has been synthesized and evaluated as orally bioavailable anti-inflammatory agents with anti-ulcerogenic activity. The anti-inflammatory and anti-ulcerogenic activities of these compounds were compared to diclofenac and omeprazole, respectively. In carrageenan-induced paw oedema assay, 2-methyl-N-((3,4-dimethoxypyridin-2-yl)methyl)-1H-benzimidazol-5-amine (12d) and 1-(1,2,3,5-tetrahydroxy-α-d-mannofuranose)-5-(((3,4-dimethoxypyridin-2yl) methyl)amino)-2-methyl-1H-benzimidazole (15d) displayed dose-dependent anti-inflammatory activities by decreasing the inflammation by 62% and 72%, respectively which is comparable to that of diclofenac (73%). In contrast to diclofenac, the anti-inflammatory activity of these compounds was not only free from any side effects on the gastric mucosa but also showed significant anti-ulcerogenic activity in rat pyloric ligation and ethanol-induced gastric ulcer models similar to that of omeprazole. Together, these findings suggest that 12d and 15d are potent anti-inflammatory agents with concurrent anti-ulcerogenic activity and support its clinical promise as a component of therapeutic strategies for inflammation, for which the gastric side effects are always a major limitation.

Double reductive amination and selective strecker reaction of a D-lyxaric aldehyde: Synthesis of diversely functionalized 3,4,5-trihydroxypiperidines

A D-mannose-derived aldehyde with the D-lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5-trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2-cyanotrihydroxypiperidines through a highly regio-and diastereoselective Strecker reaction.

An improved synthesis of a key intermediate for (+)-biotin from d-mannose

An efficient and reproducible process for the synthesis of methyl 2,3,4,5-tetradeoxy-7,8-O-isopropylidene-d-arabino-nanonate (2), a key intermediate in the total synthesis of (+)-biotin (1), starting from readily available d-mannose is described. The cruc

Chemoenzymatic synthesis of [3,9-13C]-labeled NeuAc and KDN

The chemoenzymatic synthesis of 13C-labeled sialic acid (NeuAc) and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) as useful molecular probes for studying the conformation of sialyl or KDN oligosaccharides attached to proteins was perform

A Synthetic Approach to the Squalestatins and Zaragozic Acids: Introduction of the C5 Stereocentre via an Ester-Enolate Claisen Rearrangement. The X-Ray Crystal Structure of an Intermediate

In an overall plan to synthesize the anti-cholesterol agents the squalestatins and zaragozic acids, introduction of the C5 stereochemistry was achieved via an Ireland-Claisen rearrangement of the allyl ester (7) followed by methylation, which gives the es

Enantiospecific Synthesis of the Hexahydrofuran Unit of Erythroskyrine, a Pentaenoyltetramic Acid Metabolite

A hexahydrofurofuran unit suitably functionalised for incorporation into the synthesis of erythroskyrine has been prepared in homochiral form from diacetone-D-glucose.

SYNTHESES OF 1,5-DIDEOXY-1,5-IMINO-D-MANNITOL FROM D-MANNOSE AND D-GLUCOSE

Unambigous enantiospecific syntheses of 1,5-dideoxy-1,5-imino-D-mannitol (LU1, 1-deoxy-mannojirimycin) are reported (i) from D-mannose via hydrogenation of a 5-azido-5-deoxy mannose, and (ii) from D-glucose, in which the key step involves nucleophilic substitution of a trifluoromethanesulphonyl group from C-2 of D-glucose.

SYNTHESIS OF 5-AMINO-5-DEOXY-D-MANNOPYRANOSE AND 1,5-DIDEOXY-1,5-IMINO-D-MANNITOL, AND INHIBITION OF α- AND β-D-MANNOSIDASES

The title compounds and the corresponding L-gulo derivatives were synthesised in 6 steps from benzyl 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside.The Ki values, determined from inhibition studies with α-D-mannosidases from jack beans, almonds, and calf liver, and β-D-mannosidase from Aspergillus wentii, ranged from 70 to 400 μM for the mannitol derivative and from 1.2 to 20 μM for 5-amino-5-deoxy-D-mannopyranose, i.e., inhibition is E2-E4-fold stronger than with D-mannose.Marked enhancement of inhibition with increasing pH is ascribed to the ionisation of a carboxyl group at the active site, forming an ion pair with the protonated inhibitor.The inhibition equilibrium between the jack-bean enzyme and the mannose derivative was approached slowly with kapp 2.0E5 M-1.min-1.The mannose-derived inhibitor was also inhibitory against β-D-glucosidases from almonds and Asp. wentii, with Ki values only 20-150-times larger than those for the inhibition of these enzymes by 5-amino-5-deoxy-D-glucopyranose.This moderate discrimination in binding of D-gluco and D-manno derivatives is in marked contrast to the high specificity shown by the glucosidase in catalysing the hydrolysis of mannosidases.A similar low specificity with respect to binding, combined with highly specific catalysis, was also seen with the mannosidases acting on inhibitors and substrates with the D-gluco configuration.