32233-43-5

Usage

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 
• 66348-33-2 (S)-1,2,4-butanetriol 2-(1-methyl-1-methoxyethyl ether) 
• 62214-38-4 (S)-1,2-O-isopropylidene-but-3-ene-1,2-diol 
• 95422-24-5 methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate 
• 95598-71-3 (S)-4-(2-benzoyloxy)ethyl-2,2-dimethyl-1,3-dioxolane 
• 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 
• 106976-85-6 (E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol 
• 126946-52-9 ethyl (3S)-3,4-dihydroxy-3,4-O-isopropylidene-butanoate 
• 60989-80-2 (2R)-2-phenylmethoxybutane-1,4-diol 
• 77-76-9 2,2-dimethoxy-propane 
• 42890-76-6 (S)-1,2,4-butanetriol 

Downstream Products

• 71998-69-1 (S)-4-benzyloxy-1,2-butanediol 
• 95598-71-3 (S)-4-(2-benzoyloxy)ethyl-2,2-dimethyl-1,3-dioxolane 
• 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 
• 82780-39-0 (S)-4-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane 
• 115114-87-9 (2R)-2-(2-benzyloxyethyl)oxirane 
• 85960-55-0 (S)-(2-phenylmethoxyethyl)oxirane 
• 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 
• 256390-84-8 (S)-4-(hydroxymethyl)-2-phenyl-1,3-dioxane 

Relevant academic research and scientific papers

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 difluoromethyl substituted lysophosphatidic acid analogues

Lysophosphatidic acid (LPA, 1- or 2-acyl-sn-glycerol 3-phosphate) displays an intriguing cell biology that is mediated via interactions both with G-protein coupled seven transmembrane receptors and with nuclear hormone receptor PPARγ. We describe a new and efficient route to enantiomerically homogeneous lysophospholipid analogues from (S)-1,2,4-butanetriol to give two 3-difluoromethyl substituted analogues of 2-acyl-sn-glycerol 3-phosphate. These compounds are migration-blocked analogues of the liable sn-2 LPA species. Preliminary studies were conducted on a nuclear reporter assay in which monocytic cells were transfected with a luciferase construct activated by a PPARγ nuclear receptor response element and have shown that the 3-difluoromethyl substituted analogues are fully active as natural LPA.

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.

IMMUNOMODULATORY GLYCOSPHINGOLIPIDS AND METHODS OF USE THEREOF

Provided herein are a subset of alpha-galactosylceramide (alpha-GC) compounds having improved immunomodulatory activity, particularly with respect to NKT cell number and activity. Also provided herein are methods of use of such compounds, including in the modulation of NKT cells and/or activity in vivo. Further provided are combinatorial synthesis methods for generating alpha-GC compounds of specifically defined structure and thereby generating pure preparations thereof.

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

Cobalt versus Osmium: Control of Both trans and cis Selectivity in Construction of the EFG Rings of Pectenotoxin 4

Catalytic oxidative cyclisation reactions have been employed for the synthesis of the E and F rings of the complex natural product target pectenotoxin 4. The choice of metal catalyst (cobalt- or osmium-based) allowed for the formation of THF rings with either trans or cis stereoselectivity. Fragment union using a modified Julia reaction then enabled the synthesis of an advanced synthetic intermediate containing the EF and G rings of the target.

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.

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.

VITAMIN D3 DERIVATIVES AND PHARMACEUTICAL USE THEREOF

The present invention relates to vitamin D3 derivatives of the following formula, wherein each symbol has the same meaning as defined herein, and pharmaceutical or medical use thereof for treating metabolic disease, liver disease, obesity, diabetes, cardiovascular disease, or cancer in a patient in need thereof.

One-Carbon Homologation of Primary Alcohols and the Reductive Homologation of Aldehydes Involving a Jocic-Type Reaction

(Trichloromethyl)carbinols, which are formed in one operation from either alcohols or aldehydes, can be converted into primary alcohols in a Jocic-type reaction involving LiBH4. The net result is a convenient two-step, one-carbon homologation of primary alcohols or a reductive one-carbon homologation of aldehydes featuring a broad substrate scope. The method is step-economical, and it nicely complements established one-carbon homologation strategies. (Trichloromethyl)carbinols, which are formed in one operation from either alcohols or aldehydes, can be converted into primary alcohols in a Jocic-type reaction involving LiBH4. The net result is a convenient two-step, one-carbon homologation of primary alcohols or a reductive one-carbon homologation of aldehydes featuring a broad substrate scope.