5155-46-4

Upstream product

• 6304-96-7 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 1015171-23-9 methyl altropyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 

Downstream Products

• 34340-06-2 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 1128-40-1 methyl 6-deoxy-D-altroside 
• 51607-21-7 6-deoxy-D-altritol 
• 1623075-91-1 7,4'-di-O-(1-O-methyl-6-deoxy-α-D-glicopyrane-6yl)-genistein 
• 1623075-89-7 7-O-(1-O-methyl-6-deoxy-α-D-glicopyrane-6-yl)-genistein 
• 1623075-87-5 7-O-(1-O-methyl-2,3,4-tri-O-acetyl-6-deoxy-α-D-glicopyrane-6-yl)-genistein 
• 1623075-86-4 7,4'-di-O-(1-O-methyl-2,3,4-tri-O-acetyl-6-deoxy-α-D-glicopyrane-6-yl)-genistein 
• 5155-43-1 methyl 6-deoxy-α-D-glucopyranoside 
• 1221269-61-9 methyl 6-Se-benzoyl-6-deoxy-6-seleno-α-D-glucopyranoside 
• 1221269-62-0 methyl 6-Se-benzoyl-4-O-benzoyl-6-deoxy-6-seleno-α-D-glucopyranoside 
• 40777-68-2 C₂₈H₂₄O₈ 
• 6217-21-6 methyl 2,3,4-tri-O-acetyl-6-desoxy-α-D-xylo-hex-5-enopyranoside 

Relevant academic research and scientific papers

Preparation of a 1,2-isoxazolidine synthon for the synthesis of zetekitoxin AB

A synthesis of the 1,2-isoxazolidine fragment of the potent voltage gated sodium channel blocker, zetekitoxin AB is described. The synthesis utilizes an intramolecular nitrone-olefin 1,3-dipolar cycloaddition to establish the stereochemistry of the cis-1,

The synthesis of new glycoside surfactants by means of halogenated sugars. Thioethers and methyl sulfone derivatives of α-D-glucoside and α-D-mannoside

We describe an efficient synthesis of methyl 6-halogeno-6-deoxyglycosides which was performed using Ph3P-X2 in DMF solution. Carbohydrate halides could thus be isolated in high yields without preliminary protection of the secondary hydroxyl groups, and were used as intermediates for the preparation of 6-alkylthio- and 6-alkylsulfonyl-6-deoxy glycosides. These derivatives are new non-ionic chiral surfactants.

Chloromethyl Glycosides as Versatile Synthons to Prepare Glycosyloxymethyl-Prodrugs

This work investigates the addition of monosaccharides to marketed drugs to improve their pharmacokinetic properties for oral absorption. To this end, a set of chloromethyl glycoside synthons were developed to prepare a variety of glycosyloxymethyl-prodrugs derived from 5-fluorouracil, thioguanine, propofol and losartan. Drug release was studied in vitro using β-glucosidase confirming rapid conversion of the monosaccharide prodrugs to release the parent drug, formaldehyde and the monosaccharide. To showcase this prodrug approach, a glucosyloxymethyl conjugate of the tetrazole-containing drug losartan was used for in vivo experiments and showed complete release of the drug in a dog-model.

Concise synthesis of sulfoquinovose and sulfoquinovosyl diacylglycerides, and development of a fluorogenic substrate for sulfoquinovosidases

The sulfolipid sulfoquinovosyl diacylglycerol (SQDG) and its headgroup, the sulfosugar sulfoquinovose (SQ), are estimated to harbour up to half of all organosulfur in the biosphere. SQ is liberated from SQDG and related glycosides by the action of sulfoquinovosidases (SQases). We report a 10-step synthesis of SQDG that we apply to the preparation of saturated and unsaturated lipoforms. We also report an expeditious synthesis of SQ and (13C6)SQ, and X-ray crystal structures of sodium and potassium salts of SQ. Finally, we report the synthesis of a fluorogenic SQase substrate, methylumbelliferyl α-d-sulfoquinovoside, and examination of its cleavage kinetics by two recombinant SQases. These compounds will assist in dissecting the role of sulfoglycolysis in the biogeochemical sulfur cycle and understanding the molecular basis of sulfoglycolysis.

Calcium hypophosphite mediated deiodination in water: Mechanistic insights and applications in large scale syntheses of d-quinovose and d-rhamnose

The inorganic calcium hypophosphite was found to be a cheap, non-toxic, water-soluble and environmentally friendly reducing reagent for radical deiodination in water. Thorough mechanism studies revealed that calcium hypophosphite was oxidized to water insoluble calcium phosphite which was the major co-product of the deiodination reaction. Based on this observation, a practical synthesis of rare d-quinovose and d-rhamnose from cheap and commercially available materials on a hundred-mmol scale was reported.

Method for preparing 6-nitro-deoxy-triacetylmethyl glucoside

The invention discloses a method for preparing 6-nitro-deoxy-triacetylmethyl glucoside. The method comprises the following steps: S1, by taking methyl glucoside as the raw material, directly performing iodination on six primary hydroxyl groups of methyl glucoside by use of iodine, triphenylphosphine and imidazole to prepare 6-iodomethyl glucoside; S2, protecting a hydroxyl group of 6-iodomethyl glucoside by use of an acetyl group; and S3, enabling reaction between the product of S2 and sodium nitrite and phloroglucinol to obtain the target product. Physical parameters of the obtained product are consistent with descriptions of documents, and the structure is confirmed by nuclear magnetic resonance hydrogen spectrometry and nuclear magnetic resonance mass spectrometry. The method is simple and feasible in route, silica gel column chromatography is not needed after finish of each step of reaction, and the method is suitable for not only mini-preparation in a laboratory for scientific research but also industrial production amplification, and is high in efficiency and low in cost.

Synthesis of genistein coupled with sugar derivatives and their inhibitory effect on nitric oxide production in macrophages

The isoflavone genistein 1 and some derivatives modulate IL-12, TNF-α and NO production by macrophages and lung cancer cell lines, and improve the clinical signs of experimental autoimmune encephalomyelitis (EAE). Seven genistein derivatives connected at C-6 position of a sugar, such as d-glucose and d-galactose, were synthesized. The ability to modulate macrophage response was evaluated, showing variable inhibition capacity of NO and TNF-α production in J774.A1 and RAW 264.7. Five of the seven compounds were non-cytotoxic; compound 8 was more effective to inhibit NO and TNF-α production, without affecting cell viability.

Synthesis of an α-amylase inhibitor: Highly stereoselective glycosidation and regioselective manipulations of hydroxyl groups in carbohydrate derivatives

Here, we describe the efficient synthesis of α-amylase inhibitor 1. To introduce the most expensive C ring unit at a late stage in the synthesis, we developed 1,2-cis-O-glycosidation of AB and C ring intermediates. Taking advantage of the effect of non-neighboring protecting groups, reaction solvents, and temperature for the glycosidation led to high stereoselectivity and high yield of the 1,2-cis-glycoside product bearing the API skeleton. We also explored protection and deprotection methods for regioselective manipulation of hydroxyl groups in A and B ring intermediates. One-pot benzylation of the 2,3-hydroxyl groups of d-glucose under phase-transfer conditions and regioselective anomeric deacetylation with N-methylpiperazine were developed for the syntheses of A, B, and AB ring intermediates. Thus, the efficiency of the process was dramatically improved. The raw material cost of API was reduced to approximately one-third that of the original route, and the total process was decreased by six steps.

An efficient and cost-effective preparation of di-O-acetyl-d-rhamnal

We have developed a synthetic route to the frequently utilized deoxysugar building block di-O-acetyl-d-rhamnal originating from the inexpensive starting material methyl α-d-glucopyranoside. Our approach proceeds in five steps with minimal column chromatography purification needed to afford the title compound in good overall yield.

A concise synthesis of castanospermine by the use of a transannular cyclization

(Chemical Equation Presented) A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl α-D- glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyr