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

Uses

Used in Organic Synthesis:
Methyl 2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-beta-D-ribofuranoside is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of molecules with diverse properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-beta-D-ribofuranoside is used as a building block for the development of new drugs. Its ability to form various molecular structures makes it a valuable asset in the design and synthesis of novel therapeutic agents.
Used in Chemical Research:
Methyl 2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-beta-D-ribofuranoside is also utilized in chemical research to study the properties and reactions of complex organic molecules. Its crystalline solid form provides a stable platform for researchers to investigate various chemical reactions and mechanisms.

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

Downstream Products

• 86520-87-8 Methyl-1 O-isopropylidene-2,3 desoxy-5 phenylselenyl-5 β-D-ribofuranoside 
• 62819-24-3 methyl 5-azido-5-deoxy-2,3-O-isopropylidene-b-ribofuranoside 
• 23202-81-5 methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 7702-12-7 methyl-{5-[bis-(2-chloro-ethyl)-amino]-O²,O³-isopropylidene-5-deoxy-β-D-ribofuranoside}; hydrochloride 
• 158513-63-4 methyl 5-S-benzyl-2,3-O-isopropylidene-5-thio-β-D-ribofuranoside 
• 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 

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.

BIOMARKER PANEL TARGETED TO DISEASES DUE TO MULTIFACTORIAL ONTOLOGY OF GLYCOCALYX DISRUPTION

The present disclosure provides biomarkers useful as companion diagnostics for detecting glycocalyx-based disease that is amenable to treatment using compounds designed for improving the condition of the glycocalyx and/or reducing inflammation and/or oxidative damage, as well as related compositions, kits, and methods.

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.

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.

Synthesis and biological evaluation of benzo[f]indole-4,9-diones n-linked to carbohydrate chains as new type of antitumor agents

In this work, we report the synthesis of three series of carbohydrate-based benzo[f]indole-4,9-diones and amino-1,4-naphthoquinone derivatives and evaluated their cytotoxic activity against eight human cancer cell lines. Several compounds showed a promising cytotoxic activity toward the tumor cell lines (half maximal inhibitory concentration (IC50) 10.0 μM). The importance of the substitution pattern of the quinone derivatives on the antitumor activity was also discussed. 3-Carboethoxy-2-methyl-benzo[f]indole-4,9-dione derivatives were more cytotoxic than their parent compounds and amino-1,4-naphthoquinones. Unlike clinically useful anticancer agent doxorubicin, the majority of synthesized compounds did not exhibit any lytic effects against erythrocytes or normal human leukocytes.

PRMT5 INHIBITORS

The present invention provides a compound of Formula (I) or the pharmaceutically acceptable salts thereof, which are PRMT5 inhibitors.

Industrial large-scale production method of capecitabine intermediate

The invention provides an industrial large-scale production method of a capecitabine intermediate. The industrial large-scale production method adopts a one-pot production method of simultaneously adding methanol and acetone, and is a preparation method which is energy-saving, short in production period and high in yield; a method of adding low-boiling-point solvents such as ethyl acetate into dimethyl sulfoxide or pyrrolidone for reflux cooling to take away heat is adopted; and a production method of hydrolyzing while distilling is designed, the methanol and the acetone which are generated byhydrolysis are distilled out, the methanol and the acetone in water are continuously reduced, the reaction is carried out towards K3, and the reaction is complete and thorough.

The quaternization reaction of 5-o-sulfonates of methyl 2,3-o-isopropylidene-β-D-ribofuranoside with selected heterocyclic and aliphatic amines

The synthesis of N-((methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside)-5-yl) ammoniumsalts are presented. To determine the effect of the nucleophile type and outgoing group on the quaternization reaction, selected aliphatic and heterocyclic aromatic amines reacted with: methyl 2,3-O-isopropylidene-5-O-tosyl-β-D-ribofuranoside or methyl 2,3-O-isopropylidene-5-O-mesyl-β-D -ribofuranoside ormethyl 2,3-O-isopropylidene-5-O-triflyl-β-D-ribofuranosidewere performed on amicro scale. High-resolution 1H- and 13C-NMRspectraldata for all newcompoundswere recorded. Additionally, the single-crystalX-raydiffraction analysis formethyl 2,3-O-isopropylidene-5-O-mesyl-β-D-ribofuranoside and selected in silico interaction models are reported.

New glycosylated platinum(II) phthalocyanine containing ribose moiety – synthesis and photophysical properties

The synthesis and spectral characterisation of new glycoconjugated phthalonitrile connected with triazole linker via Cu(II)-mediated click reaction is reported. Treatment of azido derivative of 1-methoxy-2,3- O-isopropylidene-β-D-ribose with 4-O-propargyloxy-substituted phthalonitrile in presence copper(II) sulfate pentahydrate and sodium L-ascorbate in tert-butanol/water gave desired glycophthalonitrile with 84% yield. This precursor underwent mixed-cyclisation with the tert-butyl-substituted phthalonitrile, to afford the mono-glycosylated A3B-type platinum(II) phthalocyanine. Upon irradiation this compound could sensitise the formation of singlet oxygen in acetone, with 0.95 quantum yield by comparative method with use of 1,3-diphenylisobenzofuran (DPBF) as scavenger.

Adenosine diphosphate ribose compound, preparation method and biological activity thereof

The invention discloses an adenosine diphosphate ribose compound, which has a general formula shown as (I), wherein the definitions of all substituents are detailed in the specification. In addition,the invention also discloses a preparation method and application of the compound. The adenosine diphosphate ribose (ADPR) structural analogue provided by the invention has specific TRPM2 (transient receptor potential melastatin 2) inhibitory activity.