117371-06-9

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 133908-86-8 benzyl mannoside 
• 100-51-6 benzyl alcohol 
• 530-26-7 D-Mannose 
• 15548-45-5 (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 

Downstream Products

• 91652-64-1 (1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane 
• 140182-79-2 benzyl 6,7,8,9-tetradeoxy-2,3-O-isopropylidene-α-D-lyxo-8-nonen-4-ulopyranoside 
• 140428-23-5 benzyl 2,3-O-isopropylidene-6,7,8,9-tetradeoxy-α-D-manno-8-nonenopyranoside 
• 140428-36-0 (1R,3S,4S,5S,6R)-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-7-azabicyclo<4.4.0>decan-8-one 
• 140428-27-9 (1R,6R,8S,9S,10S)-8-benzyloxy-9,10-isopropylidenedioxy-2,7-dioxabicyclo<4.4.0>decan-3-one 
• 140428-22-4 benzyl 2,3-O-isopropylidene-6,7,8,9-tetradeoxy-4-O-trimethylsilyl-α-D-manno-8-nonenopyranoside 
• 140428-33-7 benzyl (4,6,7-trideoxy-2,3-isopropylidene-L-erythro-oct-4-enopyranosid)uronic acid 
• 140428-34-8 7-benzyloxy-10-iodo-8,9-isopropylidenedioxy-1,6-dioxaspiro<4,5>-decan-2-one 
• 140428-28-0 methyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-α-D-manno-octopyranosid)uronate 
• 140428-32-6 3-((3aS,4S,7aS)-4-Benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionic acid ethyl ester 
• 140428-35-9 3-((3aS,4S,6R,7R,7aS)-7-Amino-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionic acid ethyl ester 
• 140428-29-1 ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-α-D-talo-octopyranosid)uronate 
• 140428-25-7 methyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-α-D-lyxo-4-octulopyranosid)uronate 
• 140428-31-5 ethyl (benzyl 4-azido-4,6,7-trideoxy-2,3-O-isopropylidene-α-D-manno-octopyranosid)uronate 

Relevant academic research and scientific papers

A simple glycolipid mimic of the phosphatidylinositol mannoside core from mycobacterium tuberculosis inhibits macrophage cytokine production

Glycolipids from Mycobacterium tuberculosis have a profound impact on the innate immune response of the host. Macrophage-inducible C-type lectin (Mincle) is a pattern-recognition receptor that has been shown to bind trehalose dimycolate (TDM) from the mycobacterium and instigate intracellular signalling in the immune cell. There are structural similarities between the structures of TDM and phosphatidyl inositol mannoside (PIM). We thus hypothesized that these latter structures might also modulate an immune response in a similar manner. To test this, we synthesized a series of new mannose derivatives modified with fatty esters at the 6-position and assessed the release of inflammatory cytokines in human U937 macrophages under the induction of lipopolysaccharides (LPS) after glycolipid treatment. The results showed that the amount of two major cytokines—tumour necrosis factor (TNF)-α and interleukin (IL)-6—released from LPS-stimulated U937 cells decreased significantly when compared to a control upon treatment with the prepared glycolipids, thus indicating a reduction in cytokine production by the macrophages.

Potent glucosidase inhibitors: De-o-suifonated ponkoranol and its stereoisomer

(Figure Presented) Ponkoranol, a glucosidase inhibitor isolated from the plant Salacia reticulata, comprises a sulfonium ion with an internal sulfate counterion. An efficient synthetic route to de-O-sulfonated ponkoranol and its 5'-stereoisomer is reported, and it is shown that these compounds are potent glucosidase inhibitors that inhibit a key intestinal human glucosidase, the N-terminal catalytic domain of maltase glucoamylase, with K, values of 43 ± 3 and 15 ± 1 nM, respectively.

On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2

Subtilisin-catalyzed esterification of several enatiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated.

Enzymatic/chemical synthesis and biological evaluation of seven-membered iminocyclitols

Several polyhydroxyperhydroazepines have been obtained either by chemoenzymatic or chemical synthesis. Condensation of (±)-3-azido-2-hydroxypropanaldehyde and dihydroxyacetone phosphate (DHAP) in the presence of a DHAP dependent aldolase followed by treat

A Novel Strategy for the Synthesis of Ammonium 3-Deoxy-D-manno-2-octulosonate (Ammonium KDO) from Lower Monosaccharides. C-C Bond Construction at C6 of D-Mannose via Cobaloxime-Mediated Radical Alkyl-Alkenyl Cross Coupling

Our synthesis of ammonium 3-deoxy-D-manno-2-octulosonate (ammonium KDO, 16) from D-mannose (3) proceeds in 10 one-flask operations in 1.5-1.6percent overall yield (66percent per operation).The strategic reaction is a C-C bond construction at C6 of D-mannose via photochemically induced radical cross coupling of α-ethoxyacrylonitrile with an alkyl cobaloxime derivative of D-mannose, in aqueous ethanol without protection of carbohydrate hydroxyls.In this paper we provide full experimental details of our KDO synthesis.In addition we provide some observations and insights on vanadium-catalyzed oxidations of α-hydroxy acids to α-keto acids.

A SYNTHESIS OF AMMONIUM 3-DEOXY-D-MANNO-2-OCTULOSONATE (AMMONIUM KDO) FROM D-MANNOSE VIA COBALOXIME-MEDIATED RADICAL ALKYL-ALKENYL CROSS COUPLING

We report a synthesis of the ammonium salt of the 8-carbon monosaccharide 3-deoxy-D-manno-2-octulosonic acid (KDO) starting from D-mannose.The key C-C bond construction in our synthetic strategy is a novel alkyl cobaloxim mediated radical alkyl-alkenyl cr