4248-74-2

Basic information

• Product Name: (-)-2,3-O-ISOPROPYLIDENE-L-THREITOL 1,4-DIMETHANE SULFONATE
• Synonyms: (-)-2,3-O-ISOPROPYLIDENE-L-THREITOL 1,4-DIMETHANE SULFONATE;(-)-2,3-O-Isopropylidene-L-threitol2,3-dimethanesulfonate;[(4S,5S)-2,2-dimethyl-5-(methylsulfonyloxymethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate;methanesulfonic acid [(4S,5S)-2,2-dimethyl-5-(methylsulfonyloxymethyl)-1,3-dioxolan-4-yl]methyl ester
• CAS NO: 4248-74-2
• Molecular Formula: C₉H₁₈O₈S₂
• Molecular Weight: 318.36442
• Mol File: 4248-74-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 501.1°Cat760mmHg
• Flash Point: 256.9°C
• Appearance: /
• Density: 1.331g/cm³
• Vapor Pressure: 1.11E-09mmHg at 25°C
• Refractive Index: 1.466
• CAS DataBase Reference: (-)-2,3-O-ISOPROPYLIDENE-L-THREITOL 1,4-DIMETHANE SULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2,3-O-ISOPROPYLIDENE-L-THREITOL 1,4-DIMETHANE SULFONATE(4248-74-2)
• EPA Substance Registry System: (-)-2,3-O-ISOPROPYLIDENE-L-THREITOL 1,4-DIMETHANE SULFONATE(4248-74-2)

Safety Data

• Hazardous Substances Data: 4248-74-2(Hazardous Substances Data)

Usage

Description

(-)-2,3-O-Isopropylidene-L-threitol 1,4-dimethane sulfonate is a chemical compound that serves as a protecting group for hydroxyl groups in carbohydrates. It is derived from threitol, a four-carbon sugar alcohol, and is utilized in organic synthesis to selectively shield hydroxyl groups during reactions. The dimethane sulfonate group allows for the mild removal of the protective group, making it a valuable tool in carbohydrate chemistry.
Used in Carbohydrate Chemistry:
(-)-2,3-O-Isopropylidene-L-threitol 1,4-dimethane sulfonate is used as a protecting group for hydroxyl groups in the synthesis of complex carbohydrates and other natural products. Its application ensures that the hydroxyl groups remain intact and unreacted during the synthesis process, facilitating the selective protection and subsequent deprotection under mild conditions.

InChI:InChI=1/C9H18O8S2/c1-9(2)16-7(5-14-18(3,10)11)8(17-9)6-15-19(4,12)13/h7-8H,5-6H2,1-4H3/t7-,8-/m0/s1

Upstream product

• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 124-63-0 methanesulfonyl chloride 
• 25432-12-6 2,3-O-Isopropyliden-DL-threitol 
• 116499-08-2 dimethyl 2,2-dimethyl-1,3-dioxolane-trans-4,5-dicarboxylate 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 

Downstream Products

• 299-74-1 DL-Threitol-1,4-bis-methansulfonat 
• 32305-98-9 (-)-Diop 
• 119322-88-2 ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanamine 
• 98253-70-4 (-)-2,2-dimethyl-4,5-bis(phenylsulfanylmethyl)-1,3-dioxolane 
• 299-74-1 treosulfan 

Relevant articles and documents

Concise synthesis of: N -phosphorylated amides through three-component reactions

N-Phosphorylated amides continue to be an unparalleled asset for the development of pharmaceutical molecules, and the importance of this framework has inspired researchers to look for concise and efficient methods for the synthesis of this unit. In this work, a new strategy was developed in which a one-pot synthesis of N-phosphorylated amides was achieved by a three-component reaction with carboxylic acids, phosphorus chlorides and azides under mild reaction conditions. To our knowledge, this is the first study in which this framework was constructed through a multicomponent reaction, which is innovative, efficient and economical. This journal is

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.

Enantioselective α-Hydroxylation by Modified Salen-Zirconium(IV)-Catalyzed Oxidation of β-Keto Esters

The highly enantioselective α-hydroxylation of β-keto esters using cumene hydroperoxide (CHP) as the oxidant was realized by a chiral (1S,2S)-cyclohexanediamine backbone salen-zirconium(IV) complex as the catalyst. A variety of corresponding chiral α-hydroxy β-keto esters were obtained in excellent yields (up to 99%) and enantioselectivities (up to 98% ee). The zirconium-catalyzed enantioselective α-hydroxylation of β-keto esters was scalable, and the zirconium catalyst was recyclable. The reaction can be performed in gram scale, and corresponding chiral products were acquired in 95% yield and 99% ee.