20689-02-5

Usage

Chemical Properties

White Needles

InChI:InChI=1/C19H26O6/c1-18(2)21-11-13(23-18)14-15-16(25-19(3,4)24-15)17(22-14)20-10-12-8-6-5-7-9-12/h5-9,13-17H,10-11H2,1-4H3/t13?,14-,15?,16-,17+/m1/s1

Upstream product

• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 100-39-0 benzyl bromide 
• 7757-38-2 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 530-26-7 D-Mannose 
• 3458-28-4 D-Mannose 
• 83050-15-1 N-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyloxy)phtalimide 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 98-88-4 benzoyl chloride 
• 14642-79-6 benzyloxy-trimethylsilane 
• 94898-41-6 (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole 

Downstream Products

• 1428265-72-8 C₃₀H₃₃N₄O₈S^(1-)*Na⁽¹⁺⁾ 
• 1428265-73-9 C₃₂H₃₇N₄O₉S^(1-)*Na⁽¹⁺⁾ 
• 1428265-74-0 C₃₃H₃₉N₄O₉S^(1-)*Na⁽¹⁺⁾ 
• 1428265-75-1 C₃₂H₃₇N₄O₁₀S^(1-)*Na⁽¹⁺⁾ 
• 196859-68-4 benzyl 2,3-O-isopropylidene-5,6-O-sulfuryl-α-D-mannofuranoside 
• 1428265-76-2 C₃₀H₃₄N₄O₅ 
• 1428265-77-3 C₃₂H₃₈N₄O₆ 
• 1428265-78-4 C₃₃H₄₀N₄O₆ 
• 1428265-79-5 C₃₂H₃₈N₄O₇ 
• 1428265-80-8 C₂₀H₂₄N₄O₅ 
• 1428265-81-9 C₂₂H₂₈N₄O₆ 
• 1428265-82-0 C₂₃H₃₀N₄O₆ 
• 1428265-83-1 C₂₂H₂₈N₄O₇ 
• 937020-97-8 benzyl 2,3-O-isopropylidene-α-D-mannofuranoside 

Relevant academic research and scientific papers

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.

Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides

Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized fro

Stereoselective syntheses of polyhydroxylated azepane derivatives from sugar-based epoxyamides. Part 1: Synthesis from d-mannose

An approach to the synthesis of polyhydroxyazepane derivatives from sugar-based epoxyamides or epoxyalcohols, in which the total regioselective epoxide opening by nitrogen nucleophiles is the key step, is described. Thus, novel polyhydroxyazepane carboxamides and aminomethyl polyhydroxyazepanes, with potential pharmacological interest, are synthesized from diacetone d-mannose. Configurational assignments of the obtained products were determined.

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 new universal solid support for oligonucleotide synthesis

Starting from 2,3:5,6-di-0-isopropylidene-α-D-mannofuranose, benzyl 5,6-ditrifluoroacetamido-5,6-dideoxy-2-0-(4,4'-dimethoxytrityl)-α-D-mannofuranose was prepared and attached to a controlled pore glass to generate a new universal solid support for oligon

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

Synthese von (+)-Aspicilin mit Bausteinen aus nachwachsenden Rohstoffen

The 18-membered lichen macrolide (+)-aspicilin (1) is easily built up from compounds 14, 16, 3, and 24 following the C3 + C7 + C6 +C2 = C18 pattern (see Schemes).The synthesis requires 15 steps and gives 1 in 13percent overall yield from D-mannose (2).The