16750-06-4

Basic information

• Product Name: D-Arabino-hexopyranose, 2-deoxy-, tetraacetate, alpha-
• Synonyms: D-Arabino-hexopyranose, 2-deoxy-, tetraacetate, alpha-;1-O,3-O,4-O,6-O-Tetraacetyl-2-deoxy-α-D-glucopyranose;2-Deoxy-α-D-arabino-hexopyranose tetraacetate
• CAS NO: 16750-06-4
• Molecular Formula: C₁₄H₂₀O₉
• Molecular Weight: 332.3
• Mol File: 16750-06-4.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 401.1°Cat760mmHg
• Flash Point: 174.9°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 1.21E-06mmHg at 25°C
• Refractive Index: 1.475
• CAS DataBase Reference: D-Arabino-hexopyranose, 2-deoxy-, tetraacetate, alpha-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Arabino-hexopyranose, 2-deoxy-, tetraacetate, alpha-(16750-06-4)
• EPA Substance Registry System: D-Arabino-hexopyranose, 2-deoxy-, tetraacetate, alpha-(16750-06-4)

Safety Data

• Hazardous Substances Data: 16750-06-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H20O9/c1-7(15)19-6-12-14(22-10(4)18)11(20-8(2)16)5-13(23-12)21-9(3)17/h11-14H,5-6H2,1-4H3

Upstream product

• 154-17-6 D-2-deoxyglucose 
• 108-24-7 acetic anhydride 
• 134160-51-3 (-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 4490-94-2 3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(ethoxycarbothioyl)sulfanyl] tetrahydro-2H-pyran-4-yl-acetate 
• 100351-75-5 2-(Tetraacetyl-1-β-D-glucosylsulfonyl)-pyridin 
• 61-58-5 2-deoxy-D-arabino-hexopyranose 
• 64-19-7 acetic acid 
• 2873-29-2 D-glucal triacetate 
• 4851-64-3 phosphoric acid diethyl ester vinyl ester 
• 75-65-0 tert-butyl alcohol 
• 13299-16-6 β-D-2-deoxy-glucopyranose 

Downstream Products

• 38223-19-7 p-nitrophenyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-arabino-hexopyranoside 
• 38223-17-5 3,4,6-tri-O-acetyl-2-deoxy-1-O-p-methylphenyl-α-D-mannopyranoside 
• 111325-61-2 (2-chloro-phenyl)-(tri-O-acetyl-α-D-arabino-2-deoxy-hexopyranoside) 
• 110056-73-0 (4-chloro-phenyl)-(tri-O-acetyl-α-D-arabino-2-deoxy-hexopyranoside) 
• 111354-53-1 (4-hydroxy-phenyl)-(tri-O-acetyl-α-D-arabino-2-deoxy-hexopyranoside) 
• 111325-46-3 (3-hydroxy-phenyl)-(tri-O-acetyl-α-D-arabino-2-deoxy-hexopyranoside) 
• 20196-78-5 1-O-phenyl-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside 
• 115408-35-0 phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-seleno-β-D-arabino-hexopyranoside 
• 115408-34-9 phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-seleno-α-D-arabino-hexopyranoside 
• 5116-45-0 1-(2-deoxy-β-D-arabino-hexopyranosyl)thymine 
• 459448-76-1 1-(3-azido-2,3-dideoxy-6-O-trityl-β-D-ribo-hexopyranosyl)thymine 
• 459448-77-2 1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione 

Relevant articles and documents

Five unusual natural carbohydrates from Actinosynnema pretiosum

Five unusual hexose derivatives were isolated from the carbohydrate portion of the solid-state fermentation extract of Actinosynnema pretiosum ssp. auranticum ATCC 31565, which is a producing strain of maytansinoids that are a family of 19-membered macrocyclic lactams having extraordinary cytotoxic and antineoplastic activities. Their structures were determined to be 2-deoxy-α-D-arabino-hexopyranose (1), 2-deoxy-β-D-arabino- hexopyranose (2), 3,6-anhydro-2-deoxy-α-D-arabino-hexcofuranose (3), 3,6-anhydro-2-deoxy-β-D-arabino-hexofuranose (4), and 2-(D-glycerol-1,2- dihydroxyethyl)furan (5) by NMR spectroscopic experiments. Springer Science+Business Media, Inc. 2008.

Exploring anomeric glycosylation of phosphoric acid: Optimisation and scope for non-native substrates

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NaBH3CN: A janus substitute for tin-free radical-based reactions

Beside showing that thermal radical reactions (reduction, Giese reaction) are efficient if bromo-/iodosugars are treated with NaBH3CN and 2,2″-azobisisobutyronitrile, we explored new initiation conditions on the basis of CuI salts (≤0.5 equiv.) supposed to produce radicals from organobromides through a set. This was confirmed, as at about 50 C under an inert atmosphere acetobromoglucose was reduced to the rearranged 2-deoxyglucose and as N-allyl α-bromoamides reacted, depending on the conditions, either by reductive cyclization or atom-transfer radical cyclization. A related cyclization occurred upon using Cu(OAc)2. This and other assays showed the reduction by NaBH3CN of CuII salts, either added or formed in situ. Having both ionic and radical reactivity, NaBH 3CN appears as a Janus reagent that may be useful for tin-free radical chemistry under mild and very simple conditions. Copyright

NaBH3CN and other systems as substitutes of tin and silicon hydrides in the light or heat-initiated reduction of halosugars: A tunable access to either 2-deoxy sugars or 1,5-anhydro-itols

UV light-promoted reduction of acetobromoglucose by NaBH3CN in t-BuOH afforded 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose in high yield and purity, via a Surzur-Tanner rearrangement, while, with 10 mol % thiophenol added, acetylated 1,5-anhydro-d-glucitol was cleanly obtained. Such tin-free and mild reductions, presumed to proceed via radical pathways, were more efficient with NaBH3CN compared to NaBH4 or NaBD 4, and do not occur with acetochloroglucose. Similar reductions to 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose were achieved upon heating to 80 C t-BuOH or CH3CN solutions of NaBH3CN and AIBN, but with a lower selectivity due to competing ionic reactions. With other pyranosyl bromides, reductions by NaBH3CN could be tuned similarly (d-galacto), but some (d-manno, 5-thio-d-xylo) gave mainly or exclusively 1,5-anhydro-itols. Other conditions, or reagents promoting SET process, afforded also reduced products, but with lower rates or selectivities. Primary iodides were reduced readily with NaBH3CN under UV light.