23262-84-2

Usage

Uses

Used in Organic Synthesis:
2,3-O-ISOPROPYLIDENE-D-ERYTHROSE is used as a protecting group for aldehydes and ketones in organic synthesis. It is favored for its ability to prevent unwanted side reactions, ensuring the selective formation of desired products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,3-O-ISOPROPYLIDENE-D-ERYTHROSE is utilized in the synthesis of various drugs. Its protective properties allow for the controlled formation of complex molecular structures, which are essential in the development of new medications.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, 2,3-O-ISOPROPYLIDENE-D-ERYTHROSE is employed in the creation of pesticides and other agricultural chemicals. Its role in protecting reactive functional groups is crucial for the synthesis of effective and targeted agrochemicals.
Used in the Synthesis of Complex Organic Molecules:
2,3-O-ISOPROPYLIDENE-D-ERYTHROSE is also used in the assembly of intricate organic molecules. Its protective capabilities are valuable in multi-step synthesis processes, where the controlled exposure of reactive sites is necessary for successful molecule construction.
Used in Carbohydrate Chemistry:
In the field of carbohydrate chemistry, 2,3-O-ISOPROPYLIDENE-D-ERYTHROSE finds application in the study and manipulation of carbohydrate structures. Its protective function aids in the selective modification of these complex biomolecules, facilitating research and development in this area.

Upstream product

• 14133-65-4 2,3-O-isopropylidene-β-L-rhamnofuranose 
• 25494-39-7 (+/-)-Isopropyliden-2,3-erythronsaeure-lacton 
• 29884-67-1 (4R,5S)-1,2,4,5,6-Pentahydroxy-hexan-3-one 
• 67-64-1 acetone 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 58645-35-5 3,4-O-isopropylidine L-arabinopyranose 
• 5328-37-0 L-arabinose 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 533-49-3 L-erythrose 
• 185699-82-5 [4R-(4α[R^*],5α)]-2,2-dimethyl-α⁴-[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]-1,3-dioxolane-4,5-dimethanol 
• 185699-86-9 [4S-(4α,5α(S^*))]-4-[(benzoyloxy)methyl]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-1,3-dioxolane 
• 185699-85-8 [4S-(4α,5α(S^*))]-4-[(benzoyloxy)methyl]-2,2-dimethyl-5-{[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]hydroxymethyl}-1,3-dioxolane 
• 185699-87-0 [4S-(4α,5α(S^*))]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane 
• 185699-83-6 (3aR-(3aα,4α,6aα))-tetrahydro-2,2-dimethyl-4-[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]furo[3,4-d]-1,3-dioxole 

Relevant academic research and scientific papers

Chagosensine: A Riddle Wrapped in a Mystery Inside an Enigma

The marine macrolide chagosensine is supposedly distinguished by a (Z,Z)-configured 1,3-chlorodiene contained within a highly strained 16-membered lactone ring, which also incorporates two trans-2,5-disubstituted tetrahydrofuran (THF) rings; this array is unique. After our initial synthesis campaign had shown that the originally proposed structure is incorrect, the published data set was critically revisited to identify potential mis-assignments. The "northern" THF ring and the anti-configured diol in the "southern" sector both seemed to be sites of concern, thus making it plausible that a panel of eight diastereomeric chagosensine-like compounds would allow the puzzle to be solved. To meet the challenge, the preparation of the required building blocks was optimized, and a convergent strategy for their assembly was developed. A key role was played by the cobalt-catalyzed oxidative cyclization of alken-5-ol derivatives ("Mukaiyama cyclization"), which is shown to be exquisitely chemoselective for terminal alkenes, leaving even terminal alkynes (and other sites of unsaturation) untouched. Likewise, a palladium-catalyzed alkyne alkoxycarbonylation reaction with formation of an α-methylene-?-lactone proved instrumental, which had not found application in natural product synthesis before. Further enabling steps were a nickel-catalyzed "Tamaru-type" homocrotylation, stereodivergent aldehyde homologations, radical hydroindation, and palladium-catalyzed alkyne-1,2-bis-stannation. The different building blocks were assembled in a serial fashion to give the idiosyncratic chlorodienes by an unprecedented site-selective Stille coupling followed by copper-mediated tin/chlorine exchange. The macrolactones were closed under forcing Yamaguchi conditions, and the resulting products were elaborated into the targeted compound library. Yet, only one of the eight diastereomers turned out to be stable in the solvent mixture that had been used to analyze the natural product; all other isomers were prone to ring opening and/or ring expansion. In addition to this stability issue, our self-consistent data set suggests that chagosensine has almost certainly little to do with the structure originally proposed by the isolation team.

Studies towards the synthesis of ertugliflozin from L-Arabinose

A new method for the diastereoselective synthesis of enantiomerically pure ertugliflozin was developed. The crucial step involves an aldol condensation between 1-(4-chloro-3-(4-ethoxybenzyl)phenyl)ethanone and (4R,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-5-((trityloxy)methyl)-1,3-dioxolane-4-carbaldehyde, which was prepared from known 2-C-trityloxymethyl-2,3-O-isopropylidene-L-erythrose (easily accessible in three steps from L-arabinose) by standard reduction/oxidation and protection/deprotection manipulations. Dihydroxylation of the aldol condensation product and further global deprotection led to the formation of the target molecule.

Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: Ready elaboration of aza-sugar scaffolds to create diverse carbohydrate-processing enzyme probes

Representative diastereomeric, erythritol and threitol polyhydroxylated pyrrolidine imine scaffolds have been rapidly elaborated to diversely functionalized aza-sugars through highly diastereoselective organometallic (RM) additions (R = Me, Et, allyl, hex

Synthesis of dl-cis-and (4R,5R)-trans-7--5(Z)-heptenoic acid analogues as platelet thromboxane A2 receptor antagonists

The title compounds have been synthesized and their in vitro thromboxane A2(TxA2) receptor antagonist activity evaluated.Both cis and trans isomers (1,2) were shown to specifically inhibit submaximal human platelet aggregation induced by 225 nM U46619 in a dose-dependent manner with an IC50 of 1 μM.The concentration of 1 and 2 required to completely block maximal aggregation induced by 3 μM U46619 was 3 μM. thromboxane A2/ receptor antagonist/ platelet aggregation/ 1,3-dioxolane

Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems

Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidene-D-glycero-L-altro-octonate (23), could be converted in two steps into a β-lactam.

Aldol Reaction between Small Sugars. Preparation of DL-threo-2-Pentulose and DL-lyxo-3-Hexulose and their Isolation as O-Isopropylidene Derivatives

The improved diastereoselectivity obtained with strongly basic anion-exchange resin as catalyst in aldol condensation between two-, three- and four-carbon "sugars" has been utilised in the preparation of DL-threo-2-pentulose and DL-lyxo-3-hexulose, which were isolated as their O-isopropylidene derivatives.A possible reason for the observe preference of formation of the lyxo-diastereomer in condensation between glycolaldehyde and glycero-tetrulose is suggested.

SYNTHESIS OF L-(4-2H)ERYTHROSE, L-(1-13C, 5-2H)ARABINOSE AND L-(2-13C, 5-2H)ARABINOSE AND IDENTIFICATION OF THE INTERMEDIATES BY 2H AND 13C-N.M.R. SPECTROSCOPY

L-(1-13C, 5-2H)Arabinose (6D) and L-(2-13C, 5-2H)arabinose (8D) have been synthesized by degradation of 2,3-O-isopropylidene-β-L-rhamnofuranose (2) to L-(4-2H)erythrose (5β, 5αD), with subsequent chain elongation to 6D plus L-(1-13C, 5-2H)ribose (7D), the latter being converted into 8D.Intermediates were identified by complete assignment of the 13C chemical shifts employing carbon-carbon and carbon-deuterium coupling constants, deuteration shifts, differential isotope-shifts, and deuterium spectra.The anomeric carbon atoms of 2 and 2,3-O-isopropylidene-L-(1-2H)erythrose (4D) gave only single 13C resonances, suggesting that these two compounds exists in only one major anomeric configuration, clarifying previously reported work.The synthesis of 2,3-O-isopropylidene-L-(1-2H)rhamnitol (3D) facilitated the assignment of the signals in the 13C spectra of the nondeuterated analog.Specific deuterium-enrichment and the observed carbon-deuterium coupling (1JC,D ca. 22 Hz) not only served to identify the deuterated carbon atom unambiguously in 3 but also permitted assignment of closely spaced resonances.The deuterium spectrum of 2,3-O-isopropylidene-L-(4-2H)erythrofuranose (4D) showed only a single resonance, indicating preponderance of one anomer, in accord with the observation of a single C-1 resonance in the 13C spectrum.