2774-29-0

Basic information

• Product Name: 3-Deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose
• Synonyms: 3-Deoxy-1,2:5,6-di-O-isopropyliden-a-D-ribo Hexafuranos;3-Deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose;3-Deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose;3-Deoxy-1,2:5,6-di-O-isopropyliden-α-D-ribo Hexafuranose;3-Deoxy-1,2:5,6-di-O-isopropyliden-a-D-ribo Hexafuranose;1-O,2-O:5-O,6-O-Di(isopropylidene)-3-deoxy-α-D-xylo-hexofuranose;1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-gulofuranose
• CAS NO: 2774-29-0
• Molecular Formula: C₁₂H₂₀O₅
• Molecular Weight: 244.285
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 2774-29-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 78-80 °C
• Boiling Point: 291.049°C at 760 mmHg
• Flash Point: 111.989°C
• Appearance: /
• Density: 1.124g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.461
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate
• Stability: Hygroscopic
• CAS DataBase Reference: 3-Deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose(2774-29-0)
• EPA Substance Registry System: 3-Deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose(2774-29-0)

Safety Data

• Hazardous Substances Data: 2774-29-0(Hazardous Substances Data)

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

• 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 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 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 
• 162427-40-9 3-deoxygalactose (α-furanose) 
• 67-64-1 acetone 
• 2774-28-9 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 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 

Downstream Products

• 4005-46-3 3-deoxy-1,2-O-isopropylidene-D-glucose 
• 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 
• 81096-97-1 (2R,4R)-6-Benzyloxy-hexane-1,2,4-triol 
• 4005-35-0 3-Desoxy-D-galaktose 

Relevant articles and documents

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

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.

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.