81495-76-3

Basic information

• Product Name: (2R,3R)-BUTANEDIOL BIS(METHANESULFONATE), 97%
• Synonyms: (2R,3R)-BUTANEDIOL BIS(METHANESULFONATE), 97%;(2R,3R)-Butanediol dimesylate
• CAS NO: 81495-76-3
• Molecular Formula: C₆H₁₄O₆S₂
• Molecular Weight: 246.30176
• Mol File: 81495-76-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 121-125 °C
• Appearance: /
• CAS DataBase Reference: (2R,3R)-BUTANEDIOL BIS(METHANESULFONATE), 97%(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-BUTANEDIOL BIS(METHANESULFONATE), 97%(81495-76-3)
• EPA Substance Registry System: (2R,3R)-BUTANEDIOL BIS(METHANESULFONATE), 97%(81495-76-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 81495-76-3(Hazardous Substances Data)

Usage

General Description

(2R,3R)-butanediol bis(methanesulfonate) is a chemical compound with a purity of 97%. It is a derivative of butanediol, which is a type of alcohol with two hydroxyl groups. In this compound, the hydroxyl groups are reacted with methanesulfonic acid to form bis(methanesulfonate) esters. This chemical is commonly used as a reagent in organic synthesis and as a protecting group for alcohols in organic chemistry. It is also used in the pharmaceutical industry for the synthesis of various drugs and as a pharmaceutical intermediate. Additionally, (2R,3R)-butanediol bis(methanesulfonate) has been studied for its potential use as a cryoprotectant in the preservation of biological materials.

Upstream product

• 24347-58-8 (R,R)-2,3-butandiol 
• 124-63-0 methanesulfonyl chloride 
• 513-85-9 2.3-butanediol 
• 6982-25-8 d,l-2,3-butanediol 

Downstream Products

• 64896-28-2 (2S,3S)-2,3-bis(diphenylphosphino)butane 

Relevant articles and documents

Structure-Activity Relationship Study of Dexrazoxane Analogues Reveals ICRF-193 as the Most Potent Bisdioxopiperazine against Anthracycline Toxicity to Cardiomyocytes Due to Its Strong Topoisomerase IIβ Interactions

Cardioprotective activity of dexrazoxane (ICRF-187), the only clinically approved drug against anthracycline-induced cardiotoxicity, has traditionally been attributed to its iron-chelating metabolite. However, recent experimental evidence suggested that the inhibition and/or depletion of topoisomerase IIβ (TOP2B) by dexrazoxane could be cardioprotective. Hence, we evaluated a series of dexrazoxane analogues and found that their cardioprotective activity strongly correlated with their interaction with TOP2B in cardiomyocytes, but was independent of their iron chelation ability. Very tight structure-activity relationships were demonstrated on stereoisomeric forms of 4,4′-(butane-2,3-diyl)bis(piperazine-2,6-dione). In contrast to its rac-form 12, meso-derivative 11 (ICRF-193) showed a favorable binding mode to topoisomerase II in silico, inhibited and depleted TOP2B in cardiomyocytes more efficiently than dexrazoxane, and showed the highest cardioprotective efficiency. Importantly, the observed ICRF-193 cardioprotection did not interfere with the antiproliferative activity of anthracycline. Hence, this study identifies ICRF-193 as the new lead compound in the development of efficient cardioprotective agents.

Discovery of a stable macrocyclic o-aminobenzamide Hsp90 inhibitor which significantly decreases tumor volume in a mouse xenograft model

An extension of our previously reported series of macrocyclic ortho-aminobenzamide Hsp90 inhibitors is reported. Addition of a second methyl group to the tether provided analogs that show increased potency in binding as well as cell-proliferation assays and, more importantly, are stable toward microsomes. We wish to disclose the discovery of a macrocycle which showed impressive biomarker activity 24-h post dosing and which demonstrated prolonged exposure in tumors. When studied in a lung cancer xenograft model, the compound demonstrated significant tumor size reduction.

New optically active 'constrained-geometry' cyclopentadienyl-phosphine ligands and their metal complexes

Optically active cyclopentadienyl-phosphine ligands were prepared by stereoselective ring opening of spirocyclopentadienes. Optically active metal complexes were made from these new bidentate ligands. A new stereogenic center at rhodium was generated by oxidative addition reactions with high stereoselectivity. The absolute configuration of the major isomer of one rhodium complex was determined by a X-ray structure analysis.