50622-10-1

Basic information

• Product Name: (-)-1,4-DI-O-METHYL-L-THREITOL
• Synonyms: (-)-1,4-DI-O-METHYL-L-THREITOL;(S,S)-(-)-1,4-DIMETHOXY-2,3-BUTANEDIOL;(S,S)-(+)-1,4-DIMETHOXY-2,3-BUTANEDIOL;(2S,3S)-1,4-Dimethoxy-2,3-butanediol;[2S,3S,(-)]-1,4-Dimethoxy-2,3-butanediol;1-O,4-O-Dimethyl-L-threitol
• CAS NO: 50622-10-1
• Molecular Formula: C₆H₁₄O₄
• Molecular Weight: 150.17
• Mol File: 50622-10-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 28-30 °C
• Boiling Point: 263.751°C at 760 mmHg
• Flash Point: 113.313°C
• Appearance: /
• Density: 1.104g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.447
• Storage Temp.: 2-8°C
• PKA: 13.27±0.20(Predicted)
• BRN: 2322227
• CAS DataBase Reference: (-)-1,4-DI-O-METHYL-L-THREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-1,4-DI-O-METHYL-L-THREITOL(50622-10-1)
• EPA Substance Registry System: (-)-1,4-DI-O-METHYL-L-THREITOL(50622-10-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 50622-10-1(Hazardous Substances Data)

Usage

Description

(-)-1,4-DI-O-METHYL-L-THREITOL is a chiral chemical compound belonging to the family of threitol isomers. It is a derivative of threitol, a four-carbon sugar alcohol, and is known for its non-superimposable mirror image forms due to its chiral nature.

Uses

Used in Pharmaceutical Industry:
(-)-1,4-DI-O-METHYL-L-THREITOL is used as a chiral building block in organic synthesis for its ability to control the stereochemistry of reactions, which is crucial in the development of new drugs and the synthesis of biologically active compounds.
Used in Agrochemical Industry:
(-)-1,4-DI-O-METHYL-L-THREITOL is utilized as a chiral building block in the synthesis of agrochemicals, contributing to the development of effective and targeted products for agricultural applications.
Used in Production of Fine Chemicals:
(-)-1,4-DI-O-METHYL-L-THREITOL serves as a valuable starting material for the synthesis of various fine chemicals, playing a key role in the creation of specialty products across different industries.
Used in Synthesis of Natural Products:
(-)-1,4-DI-O-METHYL-L-THREITOL is employed as a starting material for the synthesis of natural products, facilitating the production of complex organic compounds that are found in nature and have potential applications in various fields.

InChI:InChI=1/C6H14O4/c1-9-3-5(7)6(8)4-10-2/h5-8H,3-4H2,1-2H3/t5-,6-/m0/s1

Upstream product

• 51064-64-3 (S,S)-(-)-4,5-Bis(methoxymethyl)-2,2-dimethyl-1,3-dioxolan 
• 35677-57-7 (4R)-4r,5t-bis-methoxymethyl-2,2-dimethyl-[1,3]dioxolane 
• 67-56-1 methanol 
• 298-18-0 (S,S)-diepoxybutane 
• 123612-41-9 1,4-di-O-methyl-2,3-di-O-(tetrahydropyran-2-yl)-L-threitol 
• 87-69-4 L-Tartaric acid 
• 74-88-4 methyl iodide 
• 172794-66-0 (4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane 

Downstream Products

• 115276-20-5 4-phenyl-3-cyclohexene-1,2-dione 1-<(2S,3S)-1,4-dimethoxy-2,3-butylene>acetal 
• 120454-71-9 (R)-3-[2-((4S,5S)-4,5-Bis-methoxymethyl-[1,3]dioxolan-2-yl)-phenyl]-heptanoic acid ethyl ester 
• 120454-76-4 (S)-3-[2-((4S,5S)-4,5-Bis-methoxymethyl-[1,3]dioxolan-2-yl)-phenyl]-heptanoic acid ethyl ester 
• 120454-66-2 (R)-3-[2-((4S,5S)-4,5-Bis-methoxymethyl-[1,3]dioxolan-2-yl)-phenyl]-butyric acid ethyl ester 
• 120454-73-1 (S)-3-[2-((4S,5S)-4,5-Bis-methoxymethyl-[1,3]dioxolan-2-yl)-phenyl]-butyric acid ethyl ester 
• 120454-75-3 (R)-3-[2-((4S,5S)-4,5-Bis-methoxymethyl-[1,3]dioxolan-2-yl)-phenyl]-3-phenyl-propionic acid ethyl ester 
• 120454-75-3 (S)-3-[2-((4S,5S)-4,5-Bis-methoxymethyl-[1,3]dioxolan-2-yl)-phenyl]-3-phenyl-propionic acid ethyl ester 
• 107968-12-7 1-((4S,5S)-4,5-Bis-methoxymethyl-2-phenyl-[1,3]dioxolan-2-yl)-ethanol 
• 122428-61-9 α-acetoxyacetophenone (2S,3S)-1,4-dimethoxy-2,3-butylene acetal 
• 141376-04-7 (4S,5S)-4,5-Bis-methoxymethyl-2-methyl-2-o-tolyl-[1,3]dioxolane 
• 172794-66-0 (4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane 
• 873799-51-0 C₂₀H₂₆O₈S₂ 
• 339151-03-0 N-(2,2-diphenyl-2-hydroxyacetyl)-(S,S)-2,3-bis(methoxymethyl)aziridine 

Relevant articles and documents

Synthesis of functionalised bicyclic α-methylene-γ-butyrolactones from 2,3-cyclohexene acetal via radical cyclisation approach

2,3-Cyclohexene acetal, wherein the acetal functionality is derived from 2R,3R(+)-tartaric acid, has been transformed regioselectively into functionalised bicyclic α-methylene-γ-butyrolactones via radical cyclisations. The radicals were derived from n-bu3-SnH reactions with secondary bromides and a tertiary nitro compound.

Synthesis of l-threitol-based crown ethers and their application as enantioselective phase transfer catalyst in Michael additions

A few new l-threitol-based lariat ethers incorporating a monoaza-15-crown-5 unit were synthesized starting from diethyl l-tartrate. These macrocycles were used as phase transfer catalysts in asymmetric Michael addition reactions under mild conditions to afford the adducts in a few cases in good to excellent enantioselectivities. The addition of 2-nitropropane to trans-chalcone, and the reaction of diethyl acetamidomalonate with β-nitrostyrene resulted in the chiral Michael adducts in good enantioselectivities (90% and 95%, respectively). The substituents of chalcone had a significant impact on the yield and enantioselectivity in the reaction of diethyl acetoxymalonate. The highest enantiomeric excess (ee) values (99% ee) were measured in the case of 4-chloro- and 4-methoxychalcone. The phase transfer catalyzed cyclopropanation reaction of chalcone and benzylidene-malononitriles using diethyl bromomalonate as the nucleophile (MIRC reaction) was also developed. The corresponding chiral cyclopropane diesters were obtained in moderate to good (up to 99%) enantioselectivities in the presence of the threitol-based crown ethers.

Chiral C2-symmetric 2,3-disubstituted aziridine and 2,6-disubstituted piperidine as chiral ligands in the addition reaction of diethylzinc with arylaldehydes

Chiral C2-symmetric 2,3-disubstituted aziridines and 2,6-disubstituted piperidines having a β-amino alcohol moiety have been successfully synthesized and their catalytic chiral induction properties have been examined in the asymmetric addition reactions of diethylzinc with arylaldehydes in hexane. When N-(2,2-diphenyl-2-hydroxyethyl)-(S,S)-2,3-bis(methoxymethyl)aziridine 11 was used as a catalytic chiral ligand, sec-alcohols having (S)-configuration formed in high yields of 86-92% but low enantiomeric excesses (ee's) of 11-13%. However, when N-(2,2-diphenyl-2-hydroxyethyl)-(R,R)-2,6-disubstituted piperidine derivatives 16 and 20 were used as the chiral ligands under the same reaction conditions, the ee's of the corresponding sec-alcohols were 20-30 and 5-6%, respectively, along with the inversion of absolute configuration. A plausible mechanism for this inversion is proposed.