84379-53-3

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-2-(2,2-DIMETHYL-[1,3]DIOXOLAN-4-YL)-ETHANOL
• CAS NO: 84379-53-3
• Molecular Formula: C₁₄H₂₀O₄
• Molecular Weight: 212.24
• Mol File: 84379-53-3.mol
• Article Data: 22

Chemical Properties

• Melting Point: 75-77 °C
• Boiling Point: 424.058°C at 760 mmHg
• Flash Point: 210.263°C
• Appearance: /
• Density: 1.238g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: 2-8°C
• PKA: 14.14±0.10(Predicted)
• CAS DataBase Reference: (+)-2-O-BENZYL-L-THREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-2-O-BENZYL-L-THREITOL(84379-53-3)
• EPA Substance Registry System: (+)-2-O-BENZYL-L-THREITOL(84379-53-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36/37
• WGK Germany: 3
• F: 3-9
• Hazardous Substances Data: 84379-53-3(Hazardous Substances Data)

Usage

Description

(+)-2-O-BENZYL-L-THREITOL is a chiral compound belonging to the class of alcohols and polyols. It possesses a non-superimposable mirror image and exists in two enantiomeric forms, with the (+)-2-O-BENZYL-L-THREITOL having a specific configuration.
Used in Pharmaceutical Industry:
(+)-2-O-BENZYL-L-THREITOL is used as a chiral resolving agent for the separation of racemic mixtures, particularly in the synthesis of pharmaceuticals. It aids in creating enantiomerically pure compounds, which are essential for the development of effective and safe medications.
Used in Agrochemical Industry:
(+)-2-O-BENZYL-L-THREITOL is used as a chiral resolving agent in the synthesis of agrochemicals, ensuring the production of enantiomerically pure compounds for agricultural applications.
Used in Organic Synthesis:
(+)-2-O-BENZYL-L-THREITOL serves as a building block in organic synthesis, contributing to the creation of various chemical compounds for different purposes.
Used in Therapeutic Applications:
(+)-2-O-BENZYL-L-THREITOL has been studied for its potential therapeutic properties, such as anti-inflammatory and antioxidant effects, indicating its possible use in the development of treatments for various health conditions.

InChI:InChI=1/C11H16O4/c12-6-10(14)11(7-13)15-8-9-4-2-1-3-5-9/h1-5,10-14H,6-8H2/t10-,11-/m0/s1

Upstream product

• 116-11-0 2-Methoxypropene 
• 84379-51-1 2-O-benzyl-L-threitol 
• 38270-72-3 dimethyl 2,3-O-benzylidene-L-tartrate 
• 67-64-1 acetone 
• 100-39-0 benzyl bromide 
• 77-76-9 2,2-dimethoxy-propane 
• 866771-99-5 [(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol 
• 100906-45-4 (5S,6S)-6-(benzyloxy)-2,2-dimethyl-1,3-dioxepan-5-ol 
• 87-91-2 diethyl (2R,3R)-tartrate 
• 100-52-7 benzaldehyde 
• 333788-78-6 (2S,3S)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-butane-1,4-diol 
• 121357-96-8 methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate 
• 340699-28-7 ethyl (2R,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate 
• 114185-07-8 ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 

Downstream Products

• 84379-59-9 2-O-benzyl-1-O-hexadecyl-3,4-O-isopropylidene-L-threitol 
• 84379-60-2 2-O-benzyl-3,4-O-isopropylidene-1-O-octadecyl-L-threitol 
• 91282-44-9 (S)-4-((S)-1-Benzyloxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane 
• 100906-42-1 2-O-benzyl-3,4-O-isopropylidene-L-threose 
• 155301-38-5 (S)-4-[(R)-1-(benzyloxy)-2-bromoethyl]-2,2-dimethyl-1,3-dioxolane 
• 115689-99-1 Methanesulfonic acid (S)-2-benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester 
• 115689-97-9 Methanesulfonic acid (S)-2-benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester 
• 115689-97-9 Methanesulfonic acid (R)-2-benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester 
• 94451-14-6 (2S,4'S)-2-Benzyloxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-ethyl acetate 
• 94451-15-7 4-O-benzoyl-2-O-benzyl-1,2-O-isopropylidene-L-threitol 
• 177957-84-5 (2S,3S)-3-(O-benzyl)-4-[O-(p-methoxy)benzyl]-1,2,3,4-butanetetraol-1,2-di-O-acetonide 
• 926653-19-2 4-[1-(4-methoxy-benzyloxy)-pent-4-ynyl]-2,2-dimethyl-[1,3]dioxolane 
• 926653-20-5 4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane 
• 926653-18-1 1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-9-(2,2-dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-non-5-yn-3-ol 

Relevant articles and documents

Synthesis of C1–C11 eribulin fragment and its diastereomeric analogues

A practical stereoselective synthesis of the central C1–C10 fragment of eribulin and its two diastereomeric analogues is developed. Our approach relied on the use of L-ascorbic acid as the starting material which allowed accessing a key intermediate with a syn diol moiety (C9 and C10 of eribulin) and a carboxylic ester group. A functionalized six membered lactone having several required hydroxyl groups was then obtained. In a number of steps, the lactone was converted to an intermediate for our key oxa-Michael reaction. A regio- and stereocontrolled intramolecular oxa-Michael reaction completed the synthesis of the C1–11 fragment having a trans-fused tetrahydropyrans with the exact stereochemistry of various hydroxyl groups, as in eribulin.

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

Facile synthesis of (2R,3S)-2-benzyloxy-3-hydroxybutyrolactone

The heterocyclic diols derived from L-dimethyl tartrate are important chiral synthons in organic synthesis. In particular, L-threosolactone and L-threosolactam structures are versatile precursors for the synthesis of biologically active molecules. Structu