74152-53-7

Basic information

• Product Name: 5,6-dideoxy-1,2-O-(1-methylethylidene)-3-O-(methylsulfonyl)hex-5-enofuranose
• CAS NO: 74152-53-7
• Molecular Formula: C₁₀H₁₆O₆S
• Molecular Weight: 264.2954
• Mol File: 74152-53-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 383.2°C at 760 mmHg
• Flash Point: 185.5°C
• Density: 1.32g/cm³
• Vapor Pressure: 9.87E-06mmHg at 25°C
• Refractive Index: 1.51
• CAS DataBase Reference: 5,6-dideoxy-1,2-O-(1-methylethylidene)-3-O-(methylsulfonyl)hex-5-enofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-dideoxy-1,2-O-(1-methylethylidene)-3-O-(methylsulfonyl)hex-5-enofuranose(74152-53-7)
• EPA Substance Registry System: 5,6-dideoxy-1,2-O-(1-methylethylidene)-3-O-(methylsulfonyl)hex-5-enofuranose(74152-53-7)

Safety Data

• Hazardous Substances Data: 74152-53-7(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 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 
• 77988-19-3 5-deoxy-1,2-O-isopropylidene-3-O-mesyl-6-O-tosyl-α-D-glucofuranose 

Relevant articles and documents

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).

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