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

Uses

(4S)-(+)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane may be used in the preparation (prop-2-ynyloxy)ethyl-tethered dioxolanes via O-propargylation. It may also be used as an intermediate in the total synthesis of rugulactone.

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 
• 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 
• 85287-65-6 3,5-dinitrobenzoate of (3S)-3,4-(isopropylidenedioxy)butan-1-ol 
• 32233-44-6 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde 
• 60989-80-2 (2R)-2-phenylmethoxybutane-1,4-diol 
• 77-76-9 2,2-dimethoxy-propane 
• 42890-76-6 (S)-1,2,4-butanetriol 
• 67-64-1 acetone 
• 3068-00-6 D,L-1,2,4-butanetriol 
• 322765-15-1 (E)-ethyl 4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate 
• 96720-07-9 (E)-ethyl 4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate 
• 126946-51-8 (R)-ethyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetate 
• 112031-10-4 methyl (R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetate 

Downstream Products

• 71998-69-1 (S)-4-benzyloxy-1,2-butanediol 
• 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 
• 139884-77-8 (S)-2,2-Dimethyl-4-(2-trityloxy-ethyl)-[1,3]dioxolane 
• 85287-64-5 (S)-butane-1,2,4-triol 2,4-acetonide 
• 5469-16-9 (3S)-hydroxy-γ-butyrolactone 
• 159517-86-9 (R)-(+)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 
• 113479-25-7 (S)-3,4-isopropylidenedioxy-butyl (4-methoxy-3-nitrobenzyl) ether 
• 95598-71-3 (S)-4-(2-benzoyloxy)ethyl-2,2-dimethyl-1,3-dioxolane 
• 195257-54-6 (4S)-4-(2-[(4-methoxybenzyl)oxy]ethyl)-2,2-dimethyl-1,3-dioxolane 
• 1101876-06-5 (S)-4-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy)benzaldehyde 

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

Intramolecular thermal stepwise [2 + 2] cycloadditions: Investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones

Fused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselective intramolecular enamine [2 + 2] cyclisation furnishing δ lactone and lactam fused cyclobutenes in good yield and excellent diastereoselectivity.