2774-29-0

Usage

Chemical Properties

Light-Yellow Liquid

Uses

An intermediate for 3-Deoxy-D-glucose

InChI:InChI=1/C12H20O5/c1-11(2)13-6-9(16-11)7-5-8-10(14-7)17-12(3,4)15-8/h7-10H,5-6H2,1-4H3/t7-,8+,9?,10+/m0/s1

Upstream product

• 2774-28-9 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 16667-96-2 Dithiocarbonic acid O-[(3aR,5S,6S,6aR)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester 
• 107-13-1 acrylonitrile 
• 10368-86-2 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 
• 3253-75-6 1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside 
• 76719-48-7 1,2:5,6-di-O-isopropylidene-3-O-trifluoroacetyl-α-D-glucofuranose 
• 6936-66-9 3-deoxy-D-xylo-hexono-1,4-lactone 
• 141-78-6 ethyl acetate 
• 79-20-9 acetic acid methyl ester 
• 2774-28-9 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 162427-40-9 3-deoxygalactose (α-furanose) 
• 67-64-1 acetone 

Downstream Products

• 4005-35-0 3-Desoxy-D-galaktose 
• 4005-46-3 3-deoxy-1,2-O-isopropylidene-D-glucose 
• 81096-97-1 (2R,4R)-6-Benzyloxy-hexane-1,2,4-triol 
• 270064-36-3 ethyl (E,4R,6R)-7-(benzyloxy)-4,6-dihydroxyhept-2-enoate 
• 116431-47-1 (3aR,5R,6aR)-5-[(benzyloxy)methyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 284031-37-4 1,3,6-trideoxy-1,6-imino-D-xylo-hexitol 
• 22323-55-3 3-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose 

Relevant academic research and scientific papers

Studies on the Total Synthesis of Antibiotic Macrolactin S: A Conventional Approach for the Synthesis of the C1-C9 and C10-C24 Fragments

The C1-C9 and C10-C24 segments of the 24-membered polyene macrolide macrolactin S were synthesized by routes involving an epoxide-ring-opening reaction, an Ohira-Bestmann alkyne formation, a chelation-controlled nucleophilic addition reaction, and a Still

An antiviral medicament for the method for the preparation of entecavir

The invention relates to a preparation method of an antiviral drug Entecavir. Taking D-glucose and acetone as starting materials, the method has advantages of easy operation, high yield, easy separation and purification, wide source of raw materials and low cost. The selectivity and stereospecificity are controlled at the beginning of a reaction to effectively inhibit the production of chiral isomer. The purification method of product is simple with high yield. A key intermediate of the reaction is 4- methylol-5- methylene cyclopentane-1,3-diol, of which 4- methylol is selectively protected by trityl chloride, and the intermediate combines with 2-amino-6-chloropurine by mitsunobu. Because of the steric hinderance effect, the protecting group can effectively protect target group and the operation is easy to carry out while removing the protecting group.

Design and synthesis of harzialactone analogues: Promising anticancer agents

New homologues of harzialactone were synthesized using D-glucose as chiral template. Wittig reaction to introduce aromatic moiety in 10 and chemoselective anomeric oxidation of 13 were used as key reactions in our synthesis. Anticancer activity of these target molecules was assessed against five cancer cell lines, P388D1, HL60, COLO-205, Zr-75-1 and HeLa. Both compound 5 and 6, showed significant activity against colon cancer (COLO-205) and cervical cancer (HeLa) and moderate with others. To the best of our knowledge, this is the first report of harzialactone analogues as potent inhibitors of human colon and cervical cancer.

One-pot stereoselective double intramolecular oxymercuration: Synthesis of four isomers of an unsymmetrical bis-tetrahydrofuran ring system

Stereoselective one-pot double intramolecular oxymercuration has been demonstrated to be the key reaction in the efficient preparation of the mono-hydroxylated bis-tetrahydrofuran ring system present in asimitrin and salzmanolin, two naturally occurring b

Formal synthesis of fostriecin by a carbohydrate-based approach

The formal synthesis of fostriecin starting from d-glucose, involves chelation-controlled addition, Wittig rearrangement, ring closing metathesis and iodomethylenation, as described.

Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors

Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-1,5-imino-D-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-D-ribo-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination. (C) 2000 Elsevier Science Ltd.

Synthesis of optically active O-protected (S)- and (R)-3-hydroxyaldehydes

(S)-3-Formyloxyaldehydes, chiral synthons for natural product synthesis were synthesized via highly stereoselective hydrogenation of the unsaturated furanose ring system derived from D-glucose or D-xylose. Alternatively, (R)-3-formyloxyaldehydes were prepared via deoxygenation of 3-hydroxyfuranoses derived from D-glucose or D-xylose.