84379-51-1

Basic information

• Product Name: (+)-2-O-BENZYL-L-THREITOL
• Synonyms: (2S,3S)-3-BENZYLOXY-BUTANE-1,2,4-TRIOL;(2S,3S)-(+)-2-BENZYLOXY-1,3,4-BUTANETRIOL;(+)-2-O-BENZYL-L-THREITOL;2-benzyloxy-1,3,4-butanetriol
• CAS NO: 84379-51-1
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.24
• Mol File: 84379-51-1.mol
• Article Data: 24

Chemical Properties

• Melting Point: 75-77 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-2-O-BENZYL-L-THREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-2-O-BENZYL-L-THREITOL(84379-51-1)
• EPA Substance Registry System: (+)-2-O-BENZYL-L-THREITOL(84379-51-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36/37
• WGK Germany: 3
• F: 3-9
• Hazardous Substances Data: 84379-51-1(Hazardous Substances Data)

Usage

General Description

(+)-2-O-Benzyl-L-threitol, also known as (+)-benzylthreitol, is a chiral compound that belongs to the family of threitol derivatives. It is a white crystalline powder with a specific rotation of +18.5°, and it has various applications in organic synthesis and chemical research. (+)-2-O-BENZYL-L-THREITOL is often used as a chiral auxiliary in asymmetric synthesis to control the stereochemistry of reactions. It can also be utilized as a building block for the synthesis of various pharmaceuticals and biologically active molecules. Additionally, (+)-2-O-benzyl-L-threitol has been studied for its potential antiviral and anti-inflammatory properties. Overall, this compound has significant importance in the field of organic chemistry and has a wide range of potential applications in pharmaceuticals and other industries.

Upstream product

• 21154-16-5 diethyl-2,3-O-benzylidene-D-tartrate 
• 100-39-0 benzyl bromide 
• 119770-87-5 (2R,3R)-diethyl 2-(benzyloxy)-3-hydroxysuccinate 
• 608-68-4 dimethyl L-tartrate 
• 100-52-7 benzaldehyde 
• 38270-70-1 dimethyl meso-2,3-O-benzylidenetartrate 
• 21154-16-5 (4R,5R)-2-Phenyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester 
• 91326-83-9 (4S,5S)-dimethyl 2-phenyl-1,3-dioxolane-4,5-dicarboxylate 
• 104333-70-2 (2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester 
• 1450667-24-9 C₂₃H₂₄O₂Si 
• 1450667-23-8 C₂₅H₂₆O₃Si 
• 35572-31-7 (4R,5R)-2-Phenyl-1,3-dioxolan-4,5-dicarbonsaeure-diethylester 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 87-91-2 diethyl (2R,3R)-tartrate 

Downstream Products

• 103959-91-7 (S)-2-(benzyloxy)-2-{(S)-1',4'-dioxaspiro[4.5]decan-2'-yl}ethan-1-ol 
• 84379-53-3 2-O-benzyl-3,4-O-isopropylidene-L-threitol 
• 100906-46-5 [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol 
• 100906-45-4 (5R,6S)-6-Benzyloxy-2,2-dimethyl-[1,3]dioxepan-5-ol 
• 183387-07-7 (3S,4S)-4-benzyloxy-tetrahydro-furan-3-ol 
• 129492-58-6 (-)-2-O-benzyl-L-glyceraldehyde 
• 107938-31-8 (2S,3S)-1,3-O-Benzylidene-2-O-benzylthreitol 
• 107938-32-9 (2S,3S)-1,2-O-Benzylidene-3-O-benzylthreitol 
• 94451-15-7 4-O-benzoyl-2-O-benzyl-1,2-O-isopropylidene-L-threitol 
• 194283-76-6 4-O-benzoyl-2-O-benzyl-L-threitol 
• 194283-77-7 Benzoic acid (2S,3S)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-butyl ester 
• 194283-82-4 (E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester 
• 194283-79-9 (E)-3-[(1S,2S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-propoxy]-acrylic acid methyl ester 
• 194283-78-8 Benzoic acid (2S,3S)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-((E)-2-methoxycarbonyl-vinyloxy)-butyl ester 

Relevant articles and documents

Synthesis and anticancer profile of novel sphingoid base-like compounds with a quaternary stereocentre

The synthesis of novel sphingoid base-like compounds with a quaternary stereocentre was achieved in a sequence featuring [3,3]-sigmatropic rearrangements and olefin cross-metathesis transformation as the key reaction steps, which were accompanied by the rational selection of suitable functional group transformations. The stereochemistry of the desired tetra-substituted carbon bearing nitrogen functionality was determined via NOESY experiments of the advanced oxazolidine-2-thiones. Cell viability experiments revealed significant antiproliferative/cytotoxic activity of the target compounds 7, ent-7 and 29 against the Jurkat cell line, with the IC50 values of 6.6 μM, 5.6 μM and 6.1 μM, respectively.

Reaction of (2S,3S)-2-benzyloxybutane-1,2,4-triol with N,N′-carbonyldiimidazole

(2S,3S)-2-Benzyloxybutane-1,2,4-triol reacted with N,N′-carbonyldiimidazole to give a mixture of the expected 1,2-carbonate and the corresponding bis-carbonate.

Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation Dedicated to Associated Professor Ladislav Knieo on the occasion of his 70th birthday

Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl l-tartrate and/or l-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group