95015-20-6

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 203630-08-4 1,5-Anhydro-4,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol 
• 100-39-0 benzyl bromide 
• 13265-84-4 D-glucal 
• 821-09-0 n-Pent-4-enyl alcohol 
• 1133981-86-8 3-O-carbamoyl-4,6-di-O-benzyl-D-glucal 
• 2873-29-2 D-glucal triacetate 
• 55628-54-1 (2R,3S,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran 

Downstream Products

• 203630-08-4 1,5-Anhydro-4,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol 
• 1187452-03-4 (Z)-(4S,5R)-1-n-butylamino-5-hydroxy-4,6-O-dibenzyl-hex-1-en-3-one 
• 1187452-02-3 (Z)-(4S,5R)-1-benzylamino-5-hydroxy-4,6-O-dibenzyl-hex-1-en-3-one 

Relevant academic research and scientific papers

Palladium-Catalyzed Reaction of Aryl Iodides and Glycal Enones: Application in the Preparation of Dapagliflozin Analogues

An efficient approach for the preparation of C-1 aryl enones from aryl iodides and glycal enones by palladium-catalyzed cross-coupling reactions under ligand-free conditions was developed. A wide range of aryl iodides bearing electron-donating and withdrawing groups underwent oxidative C-1 arylation with galactal, glucal and rhamnal enones in the presence of Pd(OAc)2 and AgNO3 under mild conditions. The protecting groups, including benzyl, acetyl, pivaloyl, and benzoyl groups, were found to be compatible under standard reaction conditions. The developed methodology was applied for the preparation of dapagliflozin analogues (SGLT-2 inhibitors). Regioselective nitration of C-1 aryl enones provides C-2 nitro aryl enones in good yields.

Development of Routes for the Stereoselective Preparation of β-Aryl- C-glycosides via C-1 Aryl Enones

A wide range of enones derived from d-glucal, d-galactal, l-rhamnal, d-rhamnal, and l-arabinal underwent Heck-coupling with various arylboronic acids bearing electron-donating and -withdrawing groups in the presence of palladium acetate and 1,10-phenanthroline. These reactions provided synthetically useful C-1 aryl enones in good yields. Many sensitive functional groups as well as protecting groups present in arylboronic acids and enones, respectively, remained intact under optimized conditions. The stereoselective hydrogenation of C-1 aryl enones with Pd-C/H2 provides the β-isomer of 2-deoxy-aryl-C-glycosides in excellent yield. The C-1 aryl enones were also used as precursors for the synthesis of 2-hydroxy-β-aryl-C-glycosides. Regioselective C-2 halogenations and vinylations of C-1 aryl enones were achieved in excellent yields.

Synthesis of dibromo compounds containing 2,6-dioxabicyclo[3.1.1]heptane similar to core moiety of thromboxane A2

Thromboxane A2, a potent platelet aggregation factor, contains a labile 2,6-dioxabicyclo[3.1.1]heptane as the core moiety. Dibromo compounds with a similar core structure were synthesized by the cyclization of tribromides derived from D-glucal.

TEMPO-Catalyzed Oxidation of 3- O-Benzylated/Silylated Glycals to the Corresponding Enones Using a PIFA-Water Reagent System

A simple, highly efficient and regiospecific method for the direct conversion of 3-O-benzylated as well as silylated glycals into the corresponding enones has been developed using PIFA-TEMPO and water reagent system. The reaction is scalable on a gram sca

Protecting group and solvent control of stereo-and chemoselectivity in glucal 3-carbamate amidoglycosylation

In the Rh2(OAc)4-catalyzed amidoglycosylation of glucal 3-carbamates, anomeric stereoselectivity and the extent of competing C3-H oxidation depend on the 4O and 6O protecting groups. Acyclic protection permits high α-anomer selectivi

Stereoselective michael-type addition of organocopper reagents to enones derived from glycals in the synthesis of 2-phosphono-α-C-glycosides

Michael-type additions of various organocopper reagents to the novel carbohydrate-derived 2-(diethoxyphosphoryl)hex-1-en-3-uloses are described. The reactions have proved to be rapid, clean and stereoselective, giving rise to the formation of 3-oxo-2-phos

Glycal-mediated synthesis of enantiomerically pure 5-substituted isoxazoles containing a differentially O-benzylated glycerol moiety

A short, glycal-mediated synthesis of new chiral 5-substituted isoxazoles bearing a differentially O-protected glycerol moiety in the side chain has been accomplished. An X-ray crystallographic structural analysis confirmed the structural assignment of th

Simple oxidation of 3-O-silylated glycals: Application in deblocking 3-0-protected glycals

A high yielding allylic oxidation of 3-O-siIylated glycals 5-10 with the reagent system PhI(OAc)2-TMSN3 is presented. The iodine(m) species generated under these conditions is a lot more effective for generating carbohydrate-derived 3-trialkylsiloxy-2,3-d

Novel Bicylic Donors for the Synthesis of 2-Deoxy-β-Glycosides

Novel bicyclic glycosyl donors have been prepared by the cycloaddition reaction of glycals with 3-thiono-2,4-pentanedione 17 followed by methylenation of the resulting ketone. Treatment of the heterocyclic donors with triflic acid in the presence of a variety of alcohol acceptors leads to the formation of β-glycosides in good yields and with excellent stereoselectivities. Desulfurization of the C-2 carbon-sulfur bonds gives the corresponding 2-deoxy-β-glycosides. This method has been extended to the synthesis of glycosidic linkages found in the aureolic acid antibiotics. Tetra-N-butylammonium triflate proved to be a useful additive in these glycosylation reactions, suggesting an important role for triflate anion in stabilizing intermediates which are formed.

Oxidation of Fully Protected Glycals by Hypervalent Iodine Reagents

A new application of organoiodine(III) is presented.Fully protected glycals are directly converted into 2,3-dihydro-4H-pyran-4-ones by benzene (PhI(OH)OTs, 1).The detailed study reveals that this conversion is independent of the rel