74152-53-7

Upstream product

• 39686-83-4 1,2-O-isopropylidene-3,5,6-tri-O-methanesulphonyl-α-D-glucofuranose 
• 67-64-1 acetone 
• 23537-38-4 1,2-O-isopropylidene-3,5,6-tri-O-mesyl-α-D-glucofuranose 

Downstream Products

• 77988-19-3 5-deoxy-1,2-O-isopropylidene-3-O-mesyl-6-O-tosyl-α-D-glucofuranose 
• 148324-13-4 6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methanesulfonyl-D-glucofuranose 
• 198706-76-2 7-O-benzyl-6-deoxy-D-xyloheptulose 
• 148324-06-5 4-benzyloxy-2(R)-formyloxybutanal 
• 94530-14-0 6-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 39798-94-2 (2S,3R,4R,5R)-4-Benzyloxy-5-vinyl-tetrahydro-furan-2,3-diol 
• 19877-13-5 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose 

Relevant academic research and scientific papers

Fast, mild, and convenient procedures for iodination and bromination of carbohydrates: reactions of organoboranes with iodine monochloride, sodium iodide, bromine, and bromine chloride

5-6-Dideoxy-1,2-O-isopropylidene-3-O-methanesulfonyl-α-D-xylo-hexafuranosene-5 (1), reacts with BH3-THF to form the tris(glycosyl)borane (2) and with dicyclohexylborane to form the dicyclohexylglycosylborane (3).The iodination and bromination of 2 and 3 has been investigated using a variety of electrophiles.Iodination of either 2 or 3 with NaI-Chloramine-T/NaOAc is complete within one minute with high percentage uptake of iodine (70-90 percent) and recovery of the iodinated sugar (4).Bromination of 2 in 15 minutes with NaBr-Chloramine-T permits a high percentage uptake of bromine (75 percent), and bromination of 3 in 15 minutes with Br2/NaOAc gives the brominated sugar (5) with a reasonably good yield (60 percent) with respect to the starting material (1).

SYNTHETIC METHODS FOR THE LARGE SCALE PRODUCTION FROM GLUCOSE OF ANALOGS OF SPHINGOSINE, AZIDOSPHINGOSINE, CERAMIDES, LACTOSYL CERAMIDES, AND GLYCOSYL PHYTOSPHINGOSINE

Synthetic methods are disclosed for the production from glucose of analogs of sphingosine, azidosphingosine, ceramides, lactosyl ceramides, glycosyl phytosphingosine, and enantiomeric derivatives of phytosphingosine and/or its homologues, for use in pharm

Synthesis of 3,5-anhydro-2-deoxy-1,4-glyconolactones by palladium(II)-catalyzed, regioselective oxycarbonylation of C5- and C6-enitols. ω-Homologation of aldoses to produce intermediates for C-glycoside/C-nucleoside synthesis

The palladium(II)-catalyzed oxycarbonylation, known with alkenols and alkenediols, is studied with optically active 4-pentenitols (-triols) 1, 7 and 5-hexenitols (-tetrols) 12, 15, 18. Efficient routes for the substrates are provided, mostly from carbohyd