4137-56-8

Basic information

• Product Name: Methyl 2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-beta-D-ribofuranoside
• Synonyms: Methyl 2,3-O-isopropylidene-5-O-toluenesulfonyl-beta-D-ribofuranoside;Methyl 2,3-O-isopropylidene-5-O-tosyl-beta-D-ribofuranoside min. 99%;Methyl ,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-beta-D-ribofuranoside;((3aR,4R,6R,6aR);-6-Methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl);METHYL 2,3-O-ISOPROPYLIDENE-5-O-(4-TOLUENESULFONYL)-BETA-D-RIBOFURANOSIDE;METHYL 2,3-O-ISOPROPYLIDENE-5-O-P-TOLYLSULFONYL-B-D-RIBOFURANOSIDE;METHYL 2,3-O-ISOPROPYLIDENE-5-O-(P-TOLYLSULFONYL)-BETA-D-RIBOFURANOSIDE
• CAS NO: 4137-56-8
• Molecular Formula: C₁₆H₂₂O₇S
• Molecular Weight: 358.41
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Carbohydrates;Carbohydrates A to;Carbohydrates M-OBiochemicals and Reagents;Monosaccharide
• Mol File: 4137-56-8.mol
• Article Data: 41

Chemical Properties

• Melting Point: 83-84°C
• Boiling Point: 475.3 °C at 760 mmHg
• Flash Point: 241.3 °C
• Appearance: Crystalline Solid
• Density: 1.33 g/cm³
• Vapor Pressure: 9.61E-09mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: −20°C
• CAS DataBase Reference: Methyl 2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-beta-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-beta-D-ribofuranoside(4137-56-8)
• EPA Substance Registry System: Methyl 2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-beta-D-ribofuranoside(4137-56-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4137-56-8(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Uses

Methyl 2,3-O-Isopropylidene-5-O-p-tolylsulfonyl-?-D-ribofuranoside (cas# 4137-56-8) is a compound useful in organic synthesis.

InChI:InChI=1/C16H22O7S/c1-10-5-7-11(8-6-10)24(17,18)20-9-12-13-14(15(19-4)21-12)23-16(2,3)22-13/h5-8,12-15H,9H2,1-4H3/t12-,13-,14-,15-/m1/s1

Upstream product

• 67-56-1 methanol 
• 50-69-1 D-ribose 
• 67-64-1 acetone 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 532-20-7 D-Ribose 
• 36468-53-8 β-D-ribofuranose 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 1824-96-0 methyl ribofuranoside 
• 10257-32-6 D-ribose 
• 77-76-9 2,2-dimethoxy-propane 
• 7473-45-2 1-O-methyl-D-ribofuranose 

Downstream Products

• 14131-76-1 2-(((4R,6R)-6-methoxy-2,2-dimethyltetrahydrofuro [3,4-d][1,3]dioxol-4-yl)methyl)isoindoline-1,3-dione 
• 144541-70-8 (3aR,4R,6aR)-4-(azidomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 345898-95-5 N-(((4S,5R)-2,2-dimethyl-5-vinyl-1 ,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide 
• 376608-75-2 2-({(3aR,4S,6R,6aS)-6-[7-chloro-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-3-yl]-2,2-dimethyltetrahydro-3aH-cyclopentadiene[d][1,3]dioxolene-4-yl}oxy)ethanol 
• 376608-74-1 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylsulfanyl)-4-pyrimidinyl]amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol 
• 274693-55-9 [3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol 
• 274693-54-8 benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate 
• 866551-95-3 ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate 
• 274693-27-5 ticagrelor 
• 220241-60-1 (3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 155899-66-4 (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 155855-51-9 tetrahydro-2,2-dimethyl-6-phenylmethyl-(3aS,4S,7R,7aS)-4,7-methano-4H-1,3-dioxolo[4,5-d][1,2]oxazine 
• 155855-53-1 (3aR,4S,6R,6aS)-6-(benzylamino)-2,2-dimethyltetrahydro-3ah-cyclopenta-[d][1,3]-dioxol-4-ol 

Relevant articles and documents

[18F]-5-Fluoro-5-deoxyribose, an efficient peptide bioconjugation ligand for positron emission tomography (PET) imaging

[18F]-5-Fluoro-5-deoxyribose ([18F]-FDR) conjugates much more rapidly than [18F]-FDG under mild reaction conditions to peptides and offers new prospects for mild and rapid bioconjugation for fluorine-18 labelling in PET imaging.

A facile ultrasound-assisted synthesis of methyl 2,3-O-isopropylidene-β-D-ribofuranoside from D-ribose and its use to prepare new 1,2,3-triazole glycoconjugates

The conversion of D-ribose into its 2,3-O-isopropylidene derivative using ultrasonic irradiation is described. The ultrasound proved to be an excellent alternative as the energy source for the reaction. Different reaction times were investigated, and shorter reaction times and high yield were achieved without the need for purification of the acetonide. The compound was then applied as the starting material in the synthesis of 23 new glycoconjugates of 1,2,3-triazole that are tethered together in different ways. The synthesized compounds were characterized by FTIR, 1H NMR, 13C NMR, and HRMS techniques.

Structure-property relationships of ribose based ionic liquids

The authors of this work have successfully synthesized a broad choice of new ribose based ionic liquids, using several varying protecting groups (methyl, ethyl, allyl and benzyl) at the various positions of the carbohydrate, as well as different quarternised N-heterocycles and different anions. These consistent variations of the carbohydrate based ionic liquids (CHILs) enabled an extensive structure-property relationship study of thermal properties, allowing the authors to prove existing trends and to find a correlation between the decomposition temperature and the structure of the CHILs.