109281-59-6

Basic information

• Product Name: (+)-2,3-O-ISOPROPYLIDENE-D-THREITOL 1,4-DIMETHANE SULFONATE
• Synonyms: (+)-2,3-O-ISOPROPYLIDENE-D-THREITOL 1,4-DIMETHANE SULFONATE;(+)-2,3-O-Isopropylidene-D-threitol-2,3-dimethanesulfonate;(+)-2,3-O-Isopropylidene-D-threitol2,3-dimethanesulfonate
• CAS NO: 109281-59-6
• Molecular Formula: C₉H₁₈O₈S₂
• Molecular Weight: 318.36442
• Mol File: 109281-59-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-2,3-O-ISOPROPYLIDENE-D-THREITOL 1,4-DIMETHANE SULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-2,3-O-ISOPROPYLIDENE-D-THREITOL 1,4-DIMETHANE SULFONATE(109281-59-6)
• EPA Substance Registry System: (+)-2,3-O-ISOPROPYLIDENE-D-THREITOL 1,4-DIMETHANE SULFONATE(109281-59-6)

Safety Data

• Hazardous Substances Data: 109281-59-6(Hazardous Substances Data)

Usage

General Description

(+)-2,3-O-ISOPROPYLIDENE-D-THREITOL 1,4-DIMETHANE SULFONATE is a chemical compound used in organic synthesis as a protecting group for aldehydes and ketones. It is commonly used to temporarily mask certain functional groups during chemical reactions to prevent unwanted reactions or to control the regioselectivity of the reaction. (+)-2,3-O-ISOPROPYLIDENE-D-THREITOL 1,4-DIMETHANE SULFONATE is often added to reactions in order to achieve specific synthetic goals and is then removed under mild conditions to yield the desired product. It is a versatile tool in organic chemistry and has been widely used in the synthesis of various natural products and pharmaceuticals.

Upstream product

• 116499-08-2 dimethyl 2,2-dimethyl-1,3-dioxolane-trans-4,5-dicarboxylate 
• 25432-12-6 2,3-O-Isopropyliden-DL-threitol 
• 124-63-0 methanesulfonyl chloride 
• 73346-74-4 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol 
• 37031-29-1 (+)-dimethyl-2,3-O-isopropylidene-D-tartrate 

Downstream Products

• 299-74-1 DL-Threitol-1,4-bis-methansulfonat 
• 1947-62-2 treosulfan 

Relevant articles and documents

Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4-diepoxybutane: Role of stereochemistry

1,2,3,4-Diepoxybutane (DEB) is a bifunctional electrophile capable of forming DNA-DNA and DNA-protein cross-links. DNA alkylation by DEB produces N7-(2′-hydroxy-3′,4′-epoxybut-1′-yl)-guanine monoadducts, which can then form 1,4-bis-(guan-7-yl)-2,3-butanediol (bis-N7G-BD) lesions. All three optical isomers of DEB are produced metabolically from 1,3-butadiene, but S,S-DEB is the most cytotoxic and genotoxic. In the present work, interstrand and intrastrand DNA-DNA cross-linking by individual DEB stereoisomers was investigated by PAGE, mass spectrometry, and stable isotope labeling. S,S-, R,R-, and meso-diepoxides were synthesized from L-dimethyl-2,3-O-isopropylidene-tartrate, D-dimethyl-2,3-O-isopropylidene- tartrate, and meso-erythritol, respectively. Total numbers of bis-N7G-BD lesions (intrastrand and interstrand) in calf thymus DNA treated separately with S,S-, R,R-, or meso-DEB (0.01-0.5 mM) were similar as determined by capillary HPLC-ESI+-MS/MS of DNA hydrolysates. However, denaturing PAGE has revealed that S,S-DEB produced the highest number of interchain cross-links in 5′-GGC-3′/3′-CCG-5′ sequences. Intrastrand adduct formation by DEB was investigated by a novel methodology based on stable isotope labeling HPLC-ESI+-MS/MS. Meso DEB treatment of DNA duplexes containing 5′-[1,7, NH2-15N3,2- 13C-G]GC-3′/3′-CCG-5′ and 5′-GGC-3′/ 3′-CC[15N3,2-13C-G]-5′ trinucleotides gave rise to comparable numbers of 1,2-intrastrand and 1,3-interstrand bis-N7G-BD cross-links, while S,S DEB produced few intrastrand lesions. R,R-DEB treated DNA contained mostly 1,3-interstrand bis-N7G-BD, along with smaller amounts of 1,2-interstrand and 1,2-intrastrand adducts. The effects of DEB stereochemistry on its ability to form DNA-DNA cross-links may be rationalized by the spatial relationships between the epoxy alcohol side chains in stereoisomeric N7-(2′-hydroxy-3′,4′-epoxybut-1′-yl)- guanine adducts and their DNA environment. Different cross-linking specificities of DEB stereoisomers provide a likely structural basis for their distinct biological activities.

Analogues of Cisplatin Derived from Diaminodeoxytetritols. Synthesis and Activity against the ADJ/PC6 Plasmacytoma in Mice

Four new analogues of the anticancer drug cisplatin have been prepared that contain a diaminodideoxytetritol derivative as the amine ligand moiety, and their acitivities have been measured against the ADJ/PC6 plasmacytoma in mice.Two of these compounds, the enantiomers of cis-dichloro(1,4-diamino-1,4-dideoxy-2,3-O-isopropylidenethreitol)platinum(II), show a higher TI value than cisplatin when administered by intraperitoneal injection and, importantly, show significant antitumor acitivity when administered orally.

Chiroptical properties of 2,2’-bioxirane

The two enantiomers of 2,2′-bioxirane were synthesized, and their chiroptical properties were thoroughly investigated in various solvents by polarimetry, vibrational circular dichroism (VCD), and Raman optical activity (ROA). Density functional theory (DFT) calculations at the B3LYP/aug-cc-pVTZ level revealed the presence of three conformers (G+, G?, and cis) with Gibbs populations of 51, 44, and 5% for the isolated molecule, respectively. The population ratios of the two main conformers were modified for solvents exhibiting higher dielectric constants (G? form decreases whereas G+ form increases). The behavior of the specific optical rotation values with the different solvents was correctly reproduced by time-dependent DFT calculations using the polarizable continuum model (PCM), except for the benzene for which explicit solvent model should be necessary. Finally, VCD and ROA spectra were perfectly reproduced by the DFT/PCM calculations for the Boltzmann-averaged G+ and G? conformers.