13039-93-5

Usage

Uses

Used in Organic Synthesis:
(4S)-2,2-Dimethyl-5β-[(4R)-2,2-dimethyl-1,3-dioxolane-4β-yl]-1,3-dioxolane-4α-carbaldehyde is used as a reagent in organic synthesis for its unique chemical structure and stereochemistry, which is crucial for the reactivity and formation of desired products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (4S)-2,2-Dimethyl-5β-[(4R)-2,2-dimethyl-1,3-dioxolane-4β-yl]-1,3-dioxolane-4α-carbaldehyde is used as an intermediate in the production of various pharmaceuticals and fine chemicals, leveraging its specific stereochemistry and reactivity to synthesize target compounds.
Used in Flavor and Fragrance Industry:
Due to its unique chemical structure, (4S)-2,2-Dimethyl-5β-[(4R)-2,2-dimethyl-1,3-dioxolane-4β-yl]-1,3-dioxolane-4α-carbaldehyde has potential applications in the flavor and fragrance industry, where it can be used as a component to create distinct scents and flavors.

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 
• 114743-85-0 methyl 3,4:5,6-di-O-isopropylidene-D-gluconate 
• 52492-60-1 1,2:3,4:5,6-tri-O-isopropylidene-δ-gluconolactone 
• 69-65-8 mannitol 
• 532-20-7 D-arabinofuranose 
• 67-64-1 acetone 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 88367-49-1 tert-Butyl-[(Z)-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-allyloxy]-diphenyl-silane 
• 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 

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 
• 2280-44-6 D-Glucose 
• 530-26-7 D-Mannose 
• 121388-53-2 1-C-(3-tert-butyl-6-hydroxyphenyl)-2,3:4,5-di-O-isopropylidene-D-manno-pentitol 
• 121388-54-3 1-C-(3-tert-butyl-6-hydroxyphenyl)-2,3:4,5-di-O-isopropylidene-D-gluco-pentitol 
• 123533-30-2 (4R,5R,4'R)-5-((2S,3R,4S)-4-Methoxy-3-phenyl-oxetan-2-yl)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl] 
• 131550-01-1 (4R,4aR,6R,7S,7aS)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-methoxy-2,2-dimethyl-7-phenyl-tetrahydro-furo[3,2-d][1,3]dioxine 
• 131549-99-0 [(4R,4aR,6R,7S,7aS)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-7-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-ylmethyl]-trimethyl-silane 

Relevant academic research and scientific papers

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

Towards stereoselective synthesis of the C(31)-C(39) and C(20)-C(27) fragments of phorboxazole A

The stereoselective synthesis of the C(31)-C(39) and C(20)-C(27) fragments of phorboxazole A (1) was achieved from commercially available and inexpensive D-mannitol. Crimmins aldol reaction and a decarboxylative Claisen-type reaction are the key steps for

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.

Cyclic Phosphonate Analogs of Hexopyranoses

Acyclic and cyclic analogs of D-glucopyranose and D-mannopyranose have been prepared in which the anomeric carbon has been replaced with a phosphorus.Base-catalyzed addition of dimethyl phosphite to di-O-isopropylidene-D-arabinose followed by recrystallization yields only the acyclic gluco-isomer, through what appears to be a selective recrystallization process.The use of diethyl phosphite under similar conditions yielded only the acyclic manno-isomer.The stereochemistry of each was ascertained through comparison of the pentaacetylated derivatives 11 and 12.For the cyclic analogs 1 and 2, synthesis consists of acid-catalyzed trimethyl phosphite addition to the carbonyl of a hydroxyl-protected open-chain D-arabinose derivative, removal of a formate ester from the 4-hydroxyl group, and base-catalyzed transesterification/cyclization.All four possible cyclic α-hydroxy phosphonate diastereomers were synthesized in roughly equal amounts.Complete separation of the gluco- and manno-isomers was accomplished, and Homonuclear two-dimensional J-spectroscopy was used to supplement standard NMR analysis in order to completely characterize the isolated diastereomers 21 and 22 and assign gluco- and manno-stereochemistry, respectively.

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.

Studies on enolization of aldehydo-aldose derivatives

Acetylation of the 2,3-O-isopropylidene derivative (1) of d-glyceraldehyde with hot acetic anhydride in the presence of sodium acetate give a mixture of (Z)- and (E)-enol acetates (2 and 3), together with the acetylated racemic aldehydrol (4) of 1. Likewise, the acyclic aldehydo 2,3:4,5-diisopropylidene acetals of d- and l-arabinose, d-xylose, and d-ribose underwent conversion into enol acetates, with the (Z) isomers preponderating, and convertible photochemically into the corresponding (E) isomers. Under other conditions of acetylation, the aldehydo derivatives were converted into the corresponding aldehydrol diacetates.

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.

N-Alkylated C-Glycosyl Amino Acid Derivatives: Synthesis by a One-Pot Four-Component Ugi Reaction

C-glycosides represent an important group of naturally occurring glycosylation derivatives but are also efficient mimetics of native O-glycosides. Here, a one-pot four-component methodology is described toward a library of N-alkylated C-glycosyl amino acid derivatives comprising seven different isopropylidene-protected carbohydrate units. The applied methodology tolerates different amines and isocyanides and provides access to Ugi products in yields up to 85 %. X-ray analysis of selected products bearing three different carbohydrate motifs and comparison of their crystal structures with similar ones deposited in Cambridge Crystallographic Database revealed that four structures adopt different conformations, mostly not typical for peptide structures. This property opens the possibility to exploit here described N-alkylated C-glycosyl amino acid derivatives as templates to access different biotic and abiotic secondary structures.