32233-43-5

Basic information

• Product Name: (4S)-(+)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
• Synonyms: (S)-1,2-ISOPROPYLIDENEBUTANE-1,2,4-TRIOL;(4S)-(+)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE;2(2,2-DIMETHYL-[1,3] DIOXOLAN-4-YL)-ETHANOL (S);(4S)-2,2-Dimethyl-1,3-Dioxolane-4-Ethanol;(4S)-(+)-4-(2-HYDROXYETHYL)-2,2-DIMETHY&;(s)-(+)-2,2-dimethyl-1,3-dioxolane-4-ethanol;1,3-dioxolane-4-ethanol,2,2-dimethyl-,(4s);(S)-2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)ethanol
• CAS NO: 32233-43-5
• Molecular Formula: C₇H₁₄O₃
• Molecular Weight: 146.18
• Product Categories: Alkohols;Chiral Building Blocks;Dioxanes & Dioxolanes;Dioxolanes;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry
• Mol File: 32233-43-5.mol
• Article Data: 99

Chemical Properties

• Boiling Point: 98 °C15 mm Hg(lit.)
• Flash Point: 213 °F
• Appearance: /liquid
• Density: 1.027 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.077mmHg at 25°C
• Refractive Index: n20/D 1.4380(lit.)
• Storage Temp.: 2-8°C
• PKA: 14.80±0.10(Predicted)
• CAS DataBase Reference: (4S)-(+)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-(+)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE(32233-43-5)
• EPA Substance Registry System: (4S)-(+)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE(32233-43-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 32233-43-5(Hazardous Substances Data)

Usage

Description

(4S)-(+)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane is a chiral organic compound characterized by its unique structure and properties. It is a derivative of 1,3-dioxolane, featuring a hydroxyethyl group at the 4-position and two methyl groups at the 2-position. (4S)-(+)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE exhibits a specific stereochemistry, with the 4S configuration and a positive optical rotation, which makes it a valuable building block in organic synthesis and a potential candidate for various applications.

Uses

Used in Pharmaceutical Industry:
(4S)-(+)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane is used as an intermediate in the total synthesis of rugulactone, a natural product with potential pharmaceutical applications. Its unique structure and chirality make it a valuable component in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
(4S)-(+)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane is used in the preparation of prop-2-ynyloxyethyl-tethered dioxolanes via O-propargylation. This process allows for the creation of new compounds with potential applications in various fields, such as materials science, pharmaceuticals, and agrochemicals.

InChI:InChI=1/C7H14O3/c1-7(2)9-5-6(10-7)3-4-8/h6,8H,3-5H2,1-2H3/t6-/m0/s1

Upstream product

• 97-67-6 (S)-Malic acid 
• 116-11-0 2-Methoxypropene 
• 72229-31-3 (S)-1,2,4-butanetriol 2-(1-ethoxy-ethyl) ether 
• 67-64-1 acetone 
• 195257-54-6 (4S)-4-(2-[(4-methoxybenzyl)oxy]ethyl)-2,2-dimethyl-1,3-dioxolane 
• 159517-86-9 (R)-(+)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 
• 116556-67-3 Methyl 3,4-O-isopropylidene-2-O-phenoxythiocarbonyl-L-threonate 
• 112031-10-4 methyl (R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetate 
• 60989-80-2 (2R)-2-phenylmethoxybutane-1,4-diol 
• 77-76-9 2,2-dimethoxy-propane 
• 126946-52-9 ethyl (3S)-3,4-dihydroxy-3,4-O-isopropylidene-butanoate 
• 106976-85-6 (E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol 
• 85287-65-6 3,5-dinitrobenzoate of (3S)-3,4-(isopropylidenedioxy)butan-1-ol 
• 105183-43-5 ((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-acetic acid 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester 

Downstream Products

• 94992-56-0 (S)-1,2-O-isopropylidene-4-O-<(4-methylphenyl)sulfonyl>-1,2,4-butanetriol 
• 32233-44-6 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde 
• 121935-06-6 (S)-2,2-Dimethyl-[1,3]dioxane-4-carbaldehyde 
• 105183-43-5 ((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-acetic acid 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester 
• 67987-67-1 (4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane 
• 85287-64-5 (S)-butane-1,2,4-triol 2,4-acetonide 
• 5469-16-9 (3S)-hydroxy-γ-butyrolactone 
• 256390-84-8 (S)-4-(hydroxymethyl)-2-phenyl-1,3-dioxane 
• 159517-86-9 (R)-(+)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 
• 860438-13-7 (S)-5-((2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)thio)-1-phenyl-1H-tetrazole 
• 625821-84-3 5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-(triphenyl-λ⁵-phosphanylidene)-pentan-2-one 
• 82430-64-6 (S)-2,2-Dimethyl-4-[3-((R)-toluene-4-sulfinyl)-propyl]-[1,3]dioxolane 
• 880344-52-5 (S)-9-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-8-methyl-3-((R)-toluene-4-sulfinyl)-nonan-4-one 
• 880344-47-8 (S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-7-((R)-toluene-4-sulfinyl)-nonane-3,6-dione 

Relevant articles and documents

A highly diastereoselective synthesis of 4-octulose and 2-deoxy-4-octulose from a D-fructose derivative

Bishydroxylation of methyl (Z)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-β-D- arabino-oct-2-ene-4-ulo-4,8-pyranosonate 1 with osmium tetraoxide proceeded with extremed high diastereoselectivity to give only methyl 4,5:6,7-di-O-isopropylidene-β-D-arabino-L-erythro-oct-4-ulo-4,8-pyranosonate 2. Configurations of the new stereogenic centers (C-2,3) in 2 were determined by degradation of the C-5,6,7,8 fragment to the well-known methyl 2,3,4-tri-O-methyl-D-(+)-erythronate 7. Transformation of 2 into the required D-arabino-L-erythro-oct-4-ulosa 10, was achieved by a methodology that implied, protection to 8, reduction of the ester group in 8 to a hydroxymethyl group in 9, and finally deprotection to the free D-arabino-L-erythro-oct-4-ulosa 10. On the other hand, epoxidation reaction on (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabino-oct-2-ene-4-ulo-4,8 -pyranose 11 afforded only the corresponding 2,3-anhydro derivative 12 with β-D-arabino-D-threo configuration, as could be demonstrated by degradation to (S)-1,2,4-trimetoxybutane 16, which synthesis is reported herein.

Synthesis of (+)-(R)-Tiruchanduramine

The absolute stereochemistry of the marine alkaloid (+)-(R)-tiruchanduramine was established via a convergent total synthesis in six steps and 15.5% overall yield from Fmoc-D-Dab(Boc)-OH.

Toward an Asymmetric Synthesis of Bistramide K

The bistramides family has shown antitumoral activity. More specifically bistramide K exhibits lower toxicity than its congeners. In this work, we describe a highly stereoselective and convergent synthesis of two building blocks of the marine metabolite b

Nickel-Catalyzed Cross-Electrophile Coupling of Alkyl Fluorides: Stereospecific Synthesis of Vinylcyclopropanes

The stereospecific reductive cross-electrophile coupling reaction of 2-vinyl-4-halotetrahydropyrans for vinylcyclopropane synthesis is reported. The nickel-catalyzed reaction occurs with both alkyl fluorides and alkyl chlorides. To the best of our knowledge, this is the first reported cross-electrophile coupling reaction of an alkyl fluoride. Ring contraction proceeds with high stereospecificity, providing selective synthesis of either diastereomer of di- and trisubstituted cyclopropanes. The utility of this methodology is demonstrated by several synthetic applications including the synthesis of the natural product dictyopterene A. 2-Vinyl-4-fluorotetrahydrofurans also undergo stereospecific ring contractions, providing access to synthetically useful hydroxymethyl cyclopropanes.