13039-93-5

Basic information

• Product Name: (4S)-2,2-Dimethyl-5β-[(4R)-2,2-dimethyl-1,3-dioxolane-4β-yl]-1,3-dioxolane-4α-carbaldehyde
• Synonyms: (4R,4'R,5S)-2,2,2',2'-Tetramethyl-4,4'-bi[1,3-dioxolane]-5-carbaldehyde;(4S)-2,2-Dimethyl-5β-[(4R)-2,2-dimethyl-1,3-dioxolane-4β-yl]-1,3-dioxolane-4α-carbaldehyde;2-O,3-O:4-O,5-O-Bis(1-methylethylidene)-D-arabinose;2-O,3-O:4-O,5-O-Diisopropylidene-D-arabino-pentose;2,3:4,5-Di-O-isopropylidene-D-arabinose;2,3:4,5-Di-O-isopropylidene-aldehydo-D-arabinose;2,3:4,5-Diisopropylidene-D-arabinose
• CAS NO: 13039-93-5
• Molecular Formula: C₁₁H₁₈O₅
• Molecular Weight: 230.26
• Mol File: 13039-93-5.mol
• Article Data: 44

Chemical Properties

• Appearance: /
• Density: 1.1168 g/mL
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (4S)-2,2-Dimethyl-5β-[(4R)-2,2-dimethyl-1,3-dioxolane-4β-yl]-1,3-dioxolane-4α-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-2,2-Dimethyl-5β-[(4R)-2,2-dimethyl-1,3-dioxolane-4β-yl]-1,3-dioxolane-4α-carbaldehyde(13039-93-5)
• EPA Substance Registry System: (4S)-2,2-Dimethyl-5β-[(4R)-2,2-dimethyl-1,3-dioxolane-4β-yl]-1,3-dioxolane-4α-carbaldehyde(13039-93-5)

Safety Data

• Hazardous Substances Data: 13039-93-5(Hazardous Substances Data)

Usage

General Description

(4S)-2,2-Dimethyl-5β-[(4R)-2,2-dimethyl-1,3-dioxolane-4β-yl]-1,3-dioxolane-4α-carbaldehyde is a complex organic compound with a molecular formula of C12H20O5. It is a dioxolane derivative with a carbaldehyde functional group. This chemical is a colorless, odorless liquid that is soluble in organic solvents and insoluble in water. It is commonly used as a reagent in organic synthesis and as an intermediate in the production of pharmaceuticals and fine chemicals. In addition, this compound has potential applications in the flavor and fragrance industry due to its unique chemical structure. The stereochemistry of this compound, with both (4S) and (4R) configurations, is important for its reactivity and biological activity.

Upstream product

• 50629-31-7 2,3:4,5-di-O-isopropylidene-D-arabinose diethyldithioacetal 
• 50866-82-5 2,3:4,5-di-O-isopropylidene-aldehydo-D-ribose 
• 1941-50-0 D-arabinose diethyl dithioacetal 
• 3969-59-3 mannitol triacetonide 
• 69-65-8 mannitol 
• 532-20-7 D-arabinofuranose 
• 67-64-1 acetone 
• 88367-49-1 tert-Butyl-[(Z)-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-allyloxy]-diphenyl-silane 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 81769-41-7 (2R,3S,4R)-5-(Phenylthio)-1,2-O-isopropylidenepentane-1,2,3,4-tetrol 
• 146986-66-5 (S)-4,5-isopropylidenedioxy-2-pentenol 
• 80532-36-1 ((2R,3S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)oxiran-2-yl)methanol 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 20585-29-9 (1S)-1-cyclohexyl-O²,O³;O⁴,O⁵-diisopropyliden-D-arabitol 
• 1028182-40-2 (R)-phenyl((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methanol 
• 20715-42-8 (S)-phenyl((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methanol 
• 34685-26-2 L-(+)-arabinose dibenzyl thioacetal 
• 32795-36-1 O²,O³;O⁴,O⁵-diisopropyliden-D-arabinose-(4-nitro-phenylhydrazone) 
• 112046-87-4 2-((Ξ)-O²,O³;O⁴,O⁵-diisopropyliden-D-arabitol-1-ylidene)-1-phenyl-butane-1,3-dione 
• 10323-20-3 D-Arabinose 
• 34980-26-2 (4S,5R,4'R)-2,2,2',2'-Tetramethyl-5-((Z)-styryl)-[4,4']bi[[1,3]dioxolanyl] 
• 34980-49-9 (4S,5R,4'R)-2,2,2',2'-Tetramethyl-5-((E)-styryl)-[4,4']bi[[1,3]dioxolanyl] 
• 220172-57-6 (E)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenone 
• 77-71-4 5,5-dimethyl-imidazolidine-2,4-dione 
• 116730-55-3 5-(D-threo-2,3,4-trihydroxybutylidene)imidazol-2,4-dione 
• 116730-53-1 5-(D-erythro-2-hydroxy-3,4-isopropylidenedioxybutylidene)imidazol-2,4-dione 
• 116730-53-1 5-[(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-eth-(Z)-ylidene]-imidazolidine-2,4-dione 

Relevant articles and documents

Chirospecific synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-immo-L-xylitol via one-pot cyclisation

The multi-protected compounds 4 and 5 were treated with 20% iodine in methanol to give 1,4-dideoxy-1,4-imino-D-arabinitol 1 and 1,4-dideoxy-1,4-imino-L-xylitol 2 directly. Iodine was an efficient catalyst for deprotection of O-isopropylidene, O-(tert-butyldimethylsilyl), N-(9-phenylfluoren-9-yl) and N-benzyloxycarbonyl groups, resulting in intramolecular cyclisation.

Stereoselective synthesis of vicinal diols by the stannous chloride-mediated reaction of unprotected hydroxyallylic stannane with carbonyl compounds

The highly stereoselective synthesis of vicinal diols was accomplished by the reaction of hydroxymethyl anion equivalents with carbonyl compounds. The reaction of hydroxyallylic stannanes with various aldehydes gave but-3-en-1,2-diols in the presence of S

Synthesis of vicinal diketoses by using a metathesis-hydroxylation-oxidation sequence

Symmetrical vicinal diuloses were prepared from 2,3:4,5-di-O-isopropylidene-D-arabinose and-L-arabinose by using methyltriphenylphosphonium bromide to convert both enantiomers into the corresponding 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-arabino-hex-1-enitols D-5 and L-5. The metathesis reactions of D-5 with itself and with L-5, respectively, by using the Hoveyda-Grubbs catalyst gave diastereomeric dec-5-enitols DD-6 and DL-6, which were dihydroxylated with osmium tetroxide to give 1,2:3,4:7,8:9,10-tetra-O-isopropylidene-protected decitols DD-7 and DL-7. Swern oxidation of the decitols afforded isopropylidene-protected deco-5,6-diuloses DD-8 and DL-8, which gave unprotected deco-5,6-diuloses DD-9 and DL-9 upon acidic cleavage of the isopropylidene groups. The structures of both diastereomers were confirmed by NMR spectroscopy and X-ray crystal structure analysis.

Stereoselective synthesis of N-benzyl conduramine F-1, N-benzyl ent-conduramine E-1, dihydroconduramine F-1 and ent-dihydroconduramine E-1

A short and stereoselective synthesis of conduramine F-1 and ent-conduramine E-1 derivatives have been achieved starting from D-mannitol using nucleophilic vinylation on imine. A concise sequence of vinylation at both ends of D-mannitol and followed by RC

A concise route to access C-glycosidic tetrazolyl analogues of Kdo as bioisosteres

Ulosonic acids are an important class of carbohydrates, including well-known representatives as 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo), 3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid (Kdn) and N-Acetylneuraminic acid (Neu5Ac). As part of the lipopolysaccharides (LPS) and capsular polysaccharides (CPS, K-antigen), these carbohydrates can be found on the surfaces of, both, Gram-positive and Gram-negative bacteria. We developed a synthetic approach to access tetrazole-derivatives of these compounds. Tetrazoles have shown to be ideal analogues for the bioisosteric replacement of carboxylic acids in several drugs, improving biological activity and pharmacokinetic properties. The presented route features indium-mediated allylation with subsequent [2 + 3]-cycloaddition as key steps, leading to tetrazole-derivative of Kdo and its corresponding C-4 epimer. The route is flexible enough to be adapted to the preparation of further tetrazole ulosonic acids.

A convenient chiron approach to (4R,5R)-5-hydroxyalkylbutan-4-olides and the corresponding 7-oxa analogues from d-(+)-mannitol via an advanced common precursor: Syntheses of (-)-muricatacin, 7-oxa-(-)-muricatacin, (4R,5R)-(-)-5-hydroxy-4-decanolide, and (4R,5R)-(-)-7-oxa-5-hydroxy-4-dodecanolide

An efficient and concise chiron approach toward the synthesis of (-)-muricatacin and its unnatural 7-oxa analogue starting from commercially available and inexpensive d-(+)-mannitol via an advanced common chiral precursor has been described. In addition, (4R,5R)-(-)-5-hydroxy-4-decanolide and (4R,5R)-(-)-7-oxa-5-hydroxy-4-dodecanolide were also synthesized to show the versatility of this synthetic strategy. The methodology involves the conversion of a common chiral intermediate, prepared from d-(+)-mannitol in six steps, to a variety of target molecules in only two steps.

Crystalline 2,3:4,5-di-O-isopropylidene-DL-arabinose diethyl dithioacetal: some reactions of acetal derivatives of arabinose.

Acetonation of the diethyl dithioacetals of D- and L-arabinose gives the corresponding 2,3:4,5-diisopropylidene acetals (2a and 2b) as oils having [alpha]D +82 and -81 degrees, respectively; in admixture, the enantiomers form a well crystallized racemate, m.p. 43-45 degrees. The initial product of acetonation is the 4,5-monoisopropylidene acetal. Demercaptalation of 2a with mercury(II) chloride-cadmium carbonate gives 2,3:4,5-di-O-isopropylidene-aldehydo-D-arabinose (5) in high yield, but the literature procedure employing mercury(II) chloride-mercury(II) oxide affords a mixture of 5 and 1,2:3,4-di-O-isopropylidene-beta-D-arabinopyranose (6). A trace of acid readily and completely converts the aldehydo derivative 5 into the cyclic diacetal 6.

Chiron approach from D-mannitol to access a diastereomer of the reported structure of an acetogenin, an amide alkaloid and a sex pheromone

A short, simple and convenient chiron approach to (3R,4S,5R)-(?)-3,5-dihydroxy-4-decanolide, a hitherto unknown diastereomer of the reported structure of a naturally occurring acetogenin, (+)-polyporolide has been accomplished starting from a commercially

Dioxalanones as synthetic intermediates. Part 6. Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-Deoxy-D-Arabino-2-Heptulosonic acid (DAH) and 2-Keto-3-Deoxy-D-Gluconic acid (KDG)

Three biosynthetically significant α-keto acids KDO (7), DAH (8) and KDG (9) have been synthesised via 5-ylidene-1,3-dioxalan-4-one intermediates formed by Wittig reactions of protected monosaccharide-derived aldehydes with the Wittig reagent (3).