16750-06-4

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 
• 4490-94-2 3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(ethoxycarbothioyl)sulfanyl] tetrahydro-2H-pyran-4-yl-acetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 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 
• 13299-16-6 β-D-2-deoxy-glucopyranose 
• 75-65-0 tert-butyl alcohol 
• 100351-75-5 2-(Tetraacetyl-1-β-D-glucosylsulfonyl)-pyridin 
• 134160-51-3 (-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one 

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 
• 120085-62-3 4,5,7-Tri-O-acetyl-2,6-anhydro-3-deoxy-2,3-didehydro-D-arabino-heptononitrile 
• 3650-56-4 phenyl 2-deoxy-α-D-arabino-hexopyranoside 
• 108488-28-4 (4-amino-phenyl)-(α-D-arabino-2-deoxy-hexopyranoside) 
• 3650-57-5 (4-chloro-phenyl)-(α-D-arabino-2-deoxy-hexopyranoside) 
• 109099-99-2 (2-chloro-phenyl)-(α-D-arabino-2-deoxy-hexopyranoside) 

Relevant academic research and scientific papers

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.

INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF

Provided are molecules capable of binding to binding pockets of Plasmodium falciparum hexose transporter (PfHT) or analogs thereof and complexes comprising the same. Also provided herein are inhibitors of PfHT, pharmaceutical compositions comprising the i

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

Organoboron-catalyzed regio- and stereoselective formation of β-2-deoxyglycosidic linkages

A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-sel

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.

Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol

A mild, stereoselective, and quick approach to accessing alkynyl and alkenyl C-glycosides via BF3?Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

DABCO: An efficient promoter for the acetylation of carbohydrates and other substances under solvent-free conditions

A simple, mild and efficient solvent-free method for the acetylation of carbohydrates, and their partially protected derivatives, as well as non-carbohydrate substances in excellent yields in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is described with the advantage of tolerance to various functional groups, short reaction time and ease of product isolation.

Erosion of stereochemical control with increasing nucleophilicity: O-glycosylation at the diffusion limit

(Chemical Equation Presented) Nucleophilic substitution reactions of 2-deoxyglycosyl donors indicated that the reactivity of the oxygen nucleophile has a significant impact on stereoselectivity. Employing ethanol as the nucleophile resulted in a 1:1 (α:β) ratio of diastereomers under SN1-like reaction conditions. Stereoselective formation of the 2-deoxy-α-O-glycoside was only observed when weaker nucleophiles, such as trifluoroethanol, were employed. The lack of stereoselectivity observed in reactions of common oxygen nucleophiles can be attributed to reaction rates of the stereochemistry-determining step that approach the diffusion limit. In this scenario, both faces of the prochiral oxocarbenium ion are subject to nucleophilic addition to afford a statistical mixture of diastereomeric products. Control experiments confirmed that all nucleophilic substitution reactions were performed under kinetic control.

Highly direct α-selective glycosylations of 3,4-o-carbonate-protected 2-deoxy-and 2,6-dideoxythioglycosides by preactivation protocol

(Chemical Equation Presented) A new efficient pre-activation method for the highly α-stereoselective glycosylation of 2-deoxysugars and 2,6-dideoxysugars has been developed using 2-deoxy- and 2,6- dideoxythioglycosides as glycosyl donors. The approach allows a wide range of glycosyl acceptors and donors to be used; the α-selectivity is very good to excellent.