70005-89-9

Usage

Uses

Used in Pharmaceutical Industry:
(4R)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE is used as a starting material for the total synthesis of protectin D1, which is a significant compound in the development of novel therapeutic agents. Its role in introducing a chiral center selectively in the carbon chain C10 is essential for the successful synthesis of this molecule.
Used in Anti-diabetic Research:
In the field of anti-diabetic drug development, (4R)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE serves as a starting material for the total synthesis of cytopiloyne. Cytopiloyne is a molecule with potential anti-diabetic properties, and the chiral center introduced by (4R)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE is crucial for its biological activity.
Used in Nucleic Acid Research:
(4R)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE is also used as a starting material in the preparation of 4-15N-amino-2-butane-1,2-diol. (4R)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE is further utilized to synthesize 15N-labeled oligodeoxynucleotides, which are essential tools in the study of nucleic acid structure, function, and interactions with other molecules. The chiral center introduced by (4R)-4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE is vital for the accurate labeling and analysis of these oligodeoxynucleotides.

InChI:InChI=1/C7H14O3/c1-7(2)9-5-6(10-7)3-4-8/h6,8H,3-5H2,1-2H3/t6-/m1/s1

Upstream product

• 70005-88-8 (R)-1,2,4-butanetriol 
• 67-64-1 acetone 
• 636-61-3 D-Malic acid 
• 322765-15-1 (E)-ethyl 4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate 
• 97-67-6 L-malic acid 
• 42890-76-6 (S)-1,2,4-butanetriol 
• 126946-51-8 (R)-ethyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetate 
• 127001-96-1 (R)-1,2-O-isopropylidene-3-butene-1,2-diol 
• 112031-10-4 methyl (R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetate 
• 159517-86-9 (R)-(+)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 
• 115114-86-8 3,4-O-isopropylidene-L-(S)-erythrulose 
• 92973-40-5 methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate 
• 116556-67-3 Methyl 3,4-O-isopropylidene-2-O-phenoxythiocarbonyl-L-threonate 
• 126946-55-2 ethyl (2rac,3S)-3,4-O-isopropylidene-2-chloro-3,4-dihydroxybutane 

Downstream Products

• 165657-75-0 (4R)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate 
• 70005-88-8 (R)-1,2,4-butanetriol 
• 1084333-30-1 2-[2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-4,6-difluoro-benzonitrile 
• 1196989-23-7 5-({2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl}sulfanyl)-1-phenyl-1H-tetrazole 
• 114828-16-9 Benzyl-[(E)-(S)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-but-2-enyl]-carbamic acid benzyl ester 
• 114828-14-7 Benzyl-[(Z)-(S)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-but-2-enyl]-carbamic acid benzyl ester 
• 114884-42-3 (4S,5S)-3-Benzyl-5-[(R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-iodo-ethyl]-4-methyl-oxazolidin-2-one 
• 114828-15-8 (4S,5R)-3-Benzyl-5-[(R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-iodo-ethyl]-4-methyl-oxazolidin-2-one 
• 114884-41-2 (4S,5R)-3-Benzyl-5-[(S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-iodo-ethyl]-4-methyl-oxazolidin-2-one 
• 114828-13-6 [(Z)-(S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-methyl-but-2-enyl]-carbamic acid benzyl ester 
• 114828-17-0 (4S,5S)-3-Benzyl-5-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4-methyl-oxazolidin-2-one 
• 67987-68-2 [2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-triphenyl-phosphonium; iodide 
• 1143519-52-1 rac-[(4S*,5R*)-2-(2-tert-butyl-4-ethoxy-pyrimidin-5-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-{4-[2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-piperazin-1-yl}-methanone 

Relevant academic research and scientific papers

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.

Stereoselective synthesis of tetrahydropyranyl diarylheptanoids (-)-centrolobine and (+)-centrolobine

A versatile chiron approach to the tetrahydropyranyl diarylheptanoid natural products (-)-centrolobine and (+)-centrolobine has been described. The use of an aldol reaction followed by reductive etherification for the formation of tetrahydropyran ring is of importance. Georg Thieme Verlag Stuttgart · New York.

Total synthesis of phorboxazole A via de novo oxazole formation: Strategy and component assembly

The phorboxazole natural products are among the most potent inhibitors of cancer cell division, but they are essentially unavailable from natural sources at present. Laboratory syntheses based upon tri-component fragment coupling strategies have been developed that provide phorboxazole A and analogues in a reliable manner and with unprecedented efficiency. This has been orchestrated to occur via the sequential or simultaneous formation of both of the natural product's oxazole moieties from two serine-derived amides, involving oxidation-cyclodehydrations. The optimized preparation of three pre-assembled components, representing carbons 3-17, 18-30, and 31-46, has been developed. This article details the design and syntheses of these three essential building blocks. The convergent coupling approach is designed to facilitate the incorporation of structural changes within each component to generate unnatural analogues, targeting those with enhanced therapeutic potential and efficacy.

Benzimidazole compound

An object of the present invention is to provide a novel chemical compound useful as a therapeutic or prophylactic agent for acid-related diseases, having an excellent inhibitory effect against gastric acid secretion, an excellent effect of maintaining the inhibitory effect against gastric acid secretion, thereby maintaining intragastric pH high for a long time, and having more safety and appropriate physicochemical stability. Provided is a compound represented by where R1 and R3 may be the same or different and each represent a hydrogen atom or a C1-C6 alkyl group; R2 represents (5,5-dimethyl-1,3-dioxan-2-yl)methoxy group, 5,7-dioxaspiro[2.5]oct-6-ylmethoxy group, 1,5,9-trioxaspiro[5.5]undec-3-ylmethoxy group, or (2,2-dimethyl-1,3-dioxan-5-yl)methoxy group; R4, R5, R6 and R7 represent a hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group or C1-C6 haloalkoxy group; and W1 represents a single bond, methylene or ethylene group, a salt thereof or a solvate of these.

On the stereochemistry of palmerolide A

Degradative studies of the anticancer macrolide palmerolide A have resulted in re-assignment of the C-7, C-10, and C-11 stereocenters.

Asymmetric 1,3-dipolar cycloaddition of nitrones with an electron-withdrawing group to allylic alcohols utilizing diisopropyl tartrate as a chiral auxiliary

The asymmetric 1,3-dipolar cycloaddition of nitrones possessing an electron-withdrawing group to allylic alcohols was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding isoxazolidines with high regio-, diastereo-, and enantioselectivity. In the case of nitrones possessing an electron-withdrawing cyano or t-butoxycarbonyl group, 1,3-dipolar cycloaddition to 2-propen-1-ol occurred to produce the corresponding 3,5-trans-isoxazolidines with high enantioselectivity. To the contrary, nitrones possessing an amide moiety afforded the corresponding optically active 3,5-cis-isoxazolidines with completely opposite diastereoselectivity. A catalytic asymmetric 1,3-dipolar cycloaddition of nitrones possessing the N,N-diisopropylamide moiety to allylic alcohols was achieved to afford di- or trisubstituted isoxazolidines with excellent enantioselectivity of up to over 99% ee. The present asymmetric 1,3-dipolar cycloaddition was applied to the synthesis for the (2S,4R)-4-hydroxyornithine derivative.

Total synthesis of the potent antitumor polyketide (-)-callystatin A

A highly convergent and efficient total synthesis of the potent antitumor polyketide (-)-callystatin A is described. The synthesis required 19 steps from N-propionyl oxazolidinone 23 and produced the desired product in 3.5% overall yield.

Rational synthesis of contra-thermodynamic spiroacetals by reductive cyclizations

A synthesis of spiroacetals was developed using a reductive cyclization strategy that leads stereoselectively to spiroacetals with a single anomeric stabilization. The method begins with the synthesis of spiro ortho esters. The ortho ester is converted to a cyano acetal. Reductive lithiation of the cyano acetal generates an axial dialkoxylithium reagent, and intramolecular cyclization produces a new ring with retention of configuration. The strategy is convergent and produces complex spiro acetals in only a few steps. The method will be useful in the synthesis of natural products and will facilitate the synthesis of previously inaccessible contra-thermodynamic acetals. Copyright

Total synthesis of (+)-phorboxazole A, a potent cytostatic agent from the sponge Phorbas sp.

A convergent total synthesis of phorboxazole A (1a), from the C(3-19), C(20-27) and C(33-46) fragments 5, 4 and 91, respectively, concentrating on stereocontrolled formation of the bonds at C(2-3), C(19-20) and C(27-28), is described. Although a coupling reaction between a macrolide ketone and the side chain substituted sulfone, at C(27-28) was not successful, a Wadsworth-Emmons olefination involving the oxane methyl ketone 4 and an oxazole produced the oxane 90 which was next coupled to 91 leading to the C(20-46) unit 100. A further coupling of 100 to 71c at C(19-20) then led to 105, ultimately, and the synthesis was completed by a macrocyclisation reaction from 105, at the C(2-3) alkene bond, followed by deprotection of 106.