35572-34-0

Basic information

• Product Name: (-)-2,3-O-BENZYLIDENE-L-THREITOL
• Synonyms: (-)-2,3-O-BENZYLIDENE-L-THREITOL;(4S,5S)-(-)-2-PHENYL-1,3-DIOXOLANE-4,5-DIMETHANOL;(R)-(-)-2-PHENYL-1,3-DIOXOLANE-4,5-DIMETHANOL;1,3-Dioxolane-4,5-dimethanol, 2-phenyl-, (4S,5S)-;(-)-2,3-O-BENZYLIDENE-L-THREITOL 98+%;(-)-2,3-0-Benzylidene-L-threitol;(-)-2-O,3-O-Benzylidene-L-threitol;(4S)-2-Phenyl-1,3-dioxolane-4β,5α-dimethanol
• CAS NO: 35572-34-0
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• Mol File: 35572-34-0.mol

Chemical Properties

• Melting Point: 72-74 °C(lit.)
• Boiling Point: 309.75°C (rough estimate)
• Flash Point: 184.3°C
• Appearance: /
• Density: 1.1922 (rough estimate)
• Vapor Pressure: 1.73E-06mmHg at 25°C
• Refractive Index: 1.5384 (estimate)
• CAS DataBase Reference: (-)-2,3-O-BENZYLIDENE-L-THREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2,3-O-BENZYLIDENE-L-THREITOL(35572-34-0)
• EPA Substance Registry System: (-)-2,3-O-BENZYLIDENE-L-THREITOL(35572-34-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 35572-34-0(Hazardous Substances Data)

Usage

Chemical Properties

WHITE FINE CRYSTALLINE POWDER

InChI:InChI=1/C11H14O4/c12-6-9-10(7-13)15-11(14-9)8-4-2-1-3-5-8/h1-5,9-13H,6-7H2/t9-,10-/m0/s1

Upstream product

• 38270-72-3 dimethyl 2,3-O-benzylidene-L-tartrate 
• 35572-31-7 (4R,5R)-2-Phenyl-1,3-dioxolan-4,5-dicarbonsaeure-diethylester 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 210418-35-2 2-({(4S,5S)-5-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-phenyl-1,3-dioxolan-4-yl}methyl)-1,3-isoindolindione 
• 223548-99-0 ((4S,5S)-5-tert-Butoxycarbonylmethoxymethyl-2-phenyl-[1,3]dioxolan-4-ylmethoxy)-acetic acid tert-butyl ester 
• 623948-16-3 (S,S)-2-phenyl-4,5-bis(butoxymethyl)-1,3-dioxolane 
• 107938-29-4 (2S,3S)-1-O-Benzyl-2,3-O-benzylidenethreitol 
• 2319-57-5 threitol 
• 81135-44-6 (2S,3R)-1,4-bis(benzyloxy)-3-bromo-2-butylbenzoate 
• 107938-35-2 (2R,3R)-2,3-O-Benzylidene-1,4-diphenylthiothreitol 
• 107938-34-1 (2R,3S)-2,3-O-Benzylidene-1-phenylthiothreitol 
• 94730-27-5 (4S,5S)-2-phenyl-4,5-di(methanesulphonyloxymethyl)-1,3-dioxolan 
• 107938-40-9 (3S,4S)-4-hydroxytetrahydrofuran-3-yl benzoate 

Relevant articles and documents

Imidazolium-based chiral ionic liquids: Synthesis and application

Synthesis of chiral ionic liquids containing an imidazole nucleus and chiral centers on N-substituents is reported. [(2S,3S)-2,3-Dihydroxybutane-1,4- bis(3-butylimidazolium)]-[bis(trifluoromethanesulfonyl)amide]2 and [(4S,5S)-2-phenyl-1,3-dioxo

Synthesis and enantiomeric selectivity of chiral crown ethers

Condensation of (4S,5S)-4,5-dihydroxymethyl-2-substituted dioxolanes with polyethylene glycols ditosylates yielded new chiral crown ethers. By potentiometry the enantioselectivity of complexing between the compounds obtained and L- and D-valine methyl ester hydrochlorides was evaluated.

Tartrate-Derived Aryl Aldehyde Acetals in the Asymmetric Directed Metalation of Chromium Tricarbonyl Arene Complexes

A series of three chromium tricarbonyl benzaldehyde acetal complexes were prepared from benzaldehyde diethyl acetal and (+)-diethyl tartrate.These compounds were ortho-lithiated by a number of bases, and the diastereoselectivity of lithiation was determined by quenching of the resulting anions with Me3SiCl.Complexes 1 and 2 were found to give moderate levels of diastereoselection, while the combination of complex 3 and 2.4 equiv of n-BuLi under equilibrating conditions gave an 86percent de of silylated products.Other electrophiles gave slightly higher de's (88percent to >/= 94percent), and all products derived from 3 were separable by column chromatography.Hydrolysis of the ortho-methylated product to the corresponding benzaldehyde complex (-)-21 as well as X-ray structural analysis of the trimethylsilylated complex demonstrated that preferential pro-R deprotonation had occurred.

Preparation of (4R,5S)-(5-methyl-2,2-dimethyl-1,3-dioxolane-4-ylmethyl)-phosphonium iodide. A synthetic approach to olguine: further model studies

The enantiomerically pure title compound ((4R,5S)-(5-methyl-2,2-dimethyl-1,3-dioxolane-4-ylmethyl)-phosphonium iodide) has been synthesized starting from (R,R)-(+)-tartaric acid.The synthesis of an oliguine analog has been carried out.Attempts have been made to improve the stereoselectivity and yield of key steps.

Selective Manipulation of Hydroxy Groups in (2S,3S)-Threitol

Systematic transformation of diethyl (2R,3R)-tartrate into a number of protected or functionalized derivatives of threitol, which are important precursors for many natural products, is carried out employing reductive and oxidative cleavage reactions of be

NOVEL (4+1) FRAGMENT COMBINATION APPROACH TO CHIRAL CYCLOPENTANOIDS FROM TARTARIC ACID

A chiral cyclopentanoid building block 29 has been synthesized in a "one pot" cyclization process from epoxides 22-25 (which are readily accessible from (R,R)-(+)-tartaric acid) with the carbanion derived from phenylthioacetonitrile (PhS-CH2-CN).

AN ECONOMICAL LARGE SCALE PREPARATION OF (2S,3S)-4,5-DIMETHYL-2-PHENYL-1,3-DIOXOLAN

An economical 5-step synthesis of (2S,3S)-4,5-dimethyl-2-phenyl-1,3-dioxolan from (2R,3R)-tartaric acid is described.