5470-85-9

Usage

General Description

2-(2-phenyl-1,3-dioxolan-4-yl)ethanol, also known as piperonal ethanol, is a chemical compound with a unique molecular structure. It is a white crystalline solid with a mild, pleasant odor. 2-(2-phenyl-1,3-dioxolan-4-yl)ethanol is commonly used in the production of pharmaceuticals and fragrances due to its aromatic properties. Additionally, 2-(2-phenyl-1,3-dioxolan-4-yl)ethanol has been investigated for its potential as a vasodilator, meaning it may help widen blood vessels and improve blood flow. Overall, this chemical has a variety of potential applications in the fields of medicine, cosmetics, and perfumery.

Upstream product

• 42890-76-6 (S)-1,2,4-butanetriol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-52-7 benzaldehyde 
• 196861-66-2 (S)-2,2,9,9-tetramethyl-5-<(trimethylsilyl)oxy>-3,8-dioxa-2,9-disiladecane 
• 70005-88-8 (R)-1,2,4-butanetriol 

Relevant academic research and scientific papers

A flexible approach to azasugars: asymmetric total syntheses of (+)-castanospermine, (+)-7-deoxy-6-epi-castanospermine, and (+)-1-epi- castanospermine

The asymmetric total synthesis of natural azasugars (+)-castanospermine, (+)-7-deoxy-6-epI-castanospermine, and synthetic (+)-1-epi-castanospermine has been accomplished in nine to ten steps from a common chiral building block (S)-8. The method features a powerful chiral relay strategy consisting of a highly diastereoselective vinylogous Mukaiyama-type reaction with either chiral or achiral aldehydes (≥ 95% de; de = diastereomeric excess) and a diastereodivergent reduction of tetramic acids, which allows formation of three continuous stereogenic centers with high diastereo-selectivities. The method also provides a flexible access to structural arrays of 5-(α-hydroxyalkyl) tetramic acids, such as 17/34, and 5-(α-hydroxyalkyl)-4-hydroxyl-2- pyrrolidinones, such as 18 and 25/35 a. The method constitutes the first realization of the challenging chiral synthons A and D and thus of the conceptually attractive retrosynthetic analysis shown in Scheme 1 in a highly enantioselective manner.

New and concise approach to (R)-α-lipoic acid

A concise enantiospecific synthesis of (S)-6,8-bis(methylsulfonyloxy)- octanoic acid (2), a ready precursor of (R)-(+)-α-lipoic acid (1), is reported. The key step of the synthesis is the coupling of the tosylate derived from (R)-malic acid with phenylpro

Stereoselection in radical cyclization of β-alkoxyvinyl sulfoxides: Synthesis of tetrahydrofuranyl allyl carbinols

Equation presented. Tetrahydrofuranyl allyl carbinols may be prepared stereoselectively via radical cyclization of β-alkoxyvinyl sulfoxides, Pummerer rearrangement, and reaction with allylstannane.

Towards the diastereoselective functionalization of non-racemic acetal derivatives of η6-arylcarbonyl complexes of tricarbonylchromium

(S)-Butane-1,2,4-triol (2) has been investigated as a potential chiral auxiliary for the formation of non-racemic acetals derived from η6-arylcarbonyl complexes of tricarbonylchromium. Predominantly the cis dioxan (5) was formed from benzaldehyde, leading to preparation of the η6-Cr(CO)3 complex (16), and of the derived complexes (23) and (24). Lithiation-electrophile quenching of these complexes gave a mixture of products arising from ortho and benzylic functionalization. Reaction of acetophenone, or of the η6-Cr(CO)3 complexes (45) or (46), with either the triol (2) or its tris(silyl) ether (15) under conditions of kinetic or thermodynamic control gave an inseparable mixture of acetals.

An enantiocontrolled synthesis of pyrrolizidines, (-)-platynecine and (-)-hadinecine

Trisubstituted allylic alcohols 13 and 14 have been converted into a single isomeric trans-oxazoline 16 via an intramolecular iodoamidation of the corresponding trichloroacetimidates, which have been elaborated into (-)-platynecine 1 and(-)-hadinecine 2 via a common intermediate pyrrolizidine.

Stereoselective syntheses and reactions of chiral oxygenated α,β-unsaturated-γ- and δ-lactones

The syntheses of the chiral α,β-unsaturated lactones (+)-5, (-)-6, (+)-8, (+)-9, and (+)-10 have been efficiently achieved from readily available starting materials. The lactone (+)-5 has been synthesized in 7 steps from (R,R)-dimethyl tartrate (38-43% overall yield). The use of (+)-5 in formal syntheses of natural (+)-asperlin 4 and advanced intermediates for (+)-olguine 2 are also reported. The lactone (-)-6 has been prepared in 5 steps from (R)-malic and (44-50% overall yield). It can be a useful precursor for the syntheses of branched chain and deoxy nucleoside analogues. The preparation of (-)-6 constitutes formal syntheses of natural (+)-eldanolide 53 and the (+)-Geissman-Waiss lactone 54 (an intermediate for the syntheses of a variety of pyrrolizidine alkaloids). The lactones (+)-8, (+)-9 and (+)-10 have been synthesized from 3,4-di-O-acetyl-L-rhamnal 58. The highly diastereoselective transformations of (+)-9 and (+)-10, through sequential conjugate nucleophilic addition and enolate reaction, into densely functionalized chiral γ-lactones 12 are also reported. Copyright (C) Elsevier Science Ltd.