35019-66-0

Usage

Uses

Used in Organic Synthesis:
(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine is used as a chiral building block for the synthesis of complex organic molecules, leveraging its unique structure and stereochemistry to create enantiomerically pure compounds.
Used in Pharmaceutical Industry:
(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine is used as a potential pharmaceutical intermediate for the development of new drugs, given its specific structural features that may offer novel therapeutic properties or improve the efficacy and selectivity of existing medications.
Used in Materials Science:
(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine is used as a component in the development of new materials with tailored properties, such as chiral catalysts, sensors, or polymers, due to its distinctive chemical and stereochemical characteristics.

InChI:InChI=1/C12H17NO2/c1-12(2)14-8-10(13)11(15-12)9-6-4-3-5-7-9/h3-7,10-11H,8,13H2,1-2H3/t10-,11-/m0/s1

Upstream product

• 4508-82-1 (+/-)-2,2-dimethyl-4r-phenyl-[1,3]dioxan-5c-ylamine 
• 51317-78-3 (1S,2S)-2-formylamino-1-phenyl-1,3-propanediol 
• 67-64-1 acetone 
• 116-11-0 2-Methoxypropene 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 102224-22-6 (4S,5S)-5-(formylamino)-2,2-dimethyl-4-phenyl-1,3-dioxane 

Downstream Products

• 36808-10-3 5-bromo-2,2-dimethyl-4-phenyl-[1,3]dioxane 
• 97036-27-6 (2R)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(2-thienyl)acetonitril 
• 97036-25-4 (2S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(2-thienyl)acetonitril 
• 97036-23-2 (4S,5S)-(+)-2,2-Dimethyl-4-phenyl-5-<(2-thienylmethylen)amino>-1,3-dioxan 
• 97036-28-7 (2S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(3-thienyl)acetonitril 
• 97036-26-5 (2R)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(3-thienyl)acetonitril 
• 97036-24-3 (4S,5S)-(+)-2,2-Dimethyl-4-phenyl-5-<(3-thienylmethylen)amino>-1,3-dioxan 
• 74491-53-5 (+)-(4S,5S)-(nicotinoylamino)-2,2-dimethyl-4-phenyl-1,3-dioxan 
• 124686-47-1 (4S,5S)-(+)-2,2-Dimethyl-5-methylamino-4-phenyl-1,3-dioxan 
• 95976-40-2 (2R,4S)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-5,5,5-trifluor-4-methylvaleronitril 
• 95911-01-6 (2R,4R)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-5,5,5-trifluor-4-methylvaleronitril 
• 95911-00-5 (2S,4S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-5,5,5-trifluor-4-methylvaleronitril 
• 95853-76-2 (2S,4R)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-5,5,5-trifluor-4-methylvaleronitril 
• 73872-14-7 (2S,4'S,5'S)-(+)-2-Amino-N-(2',2'-dimethyl-4'-phenyl-1',3'-dioxan-5'-yl)-2-phenylacetonitril 

Relevant academic research and scientific papers

A chemoenzymatic and fully stereocontrolled total synthesis of the antibacterial natural product (-)-platencin

The natural product (-)-platencin is a potent antibacterial agent that exerts its effects through a novel mode of action. As such, it is an important lead in the development of next-generation antibacterials that are urgently needed because of the rapidly developing resistance to current therapies. The work reported here concerns the development of a convergent and chemoenzymatic total synthesis of (-)-platencin by methods that should provide access to a range of biologically relevant analogues. The key step involves a thermally promoted and facially selective intramolecular Diels-Alder (IMDA) cycloaddition reaction to give an adduct that embodies the tricarbocyclic core of (-)-platencin. This adduct was elaborated over thirteen steps to the natural product. The substrate for the IMDA reaction was prepared by Stille cross-coupling of a Z-configured alkenylstannane with an iodinated diene obtained in an enantiomerically pure form through the whole-cell biotransformation of iodobenzene.

Binaphthalene-derived iminium salt catalysts for highly enantioselective asymmetrie epoxidation

Enantiomerically enriched epoxides are useful intermediates that have found many applications in asymmetric synthesis, and development of efficient catalysts for asymmetric epoxidation has received considerable attention, In this manuscript we describe the design, preparation, and use of new highly selective imlnium salt organocatalysts for asymmetric epoxidation, based around a chiral binaphthalene motif coupled with a chiral substituted dioxane moiety. The new catalysts have been tested in the catalytic asymmetric epoxidation of unfunctionalized alkenes, and provide up to 95 % ee.

New chiral iminium salt catalysts for asymmetric epoxidation

A range of enantiomerically pure 4-substituted 5-amino-1,3-dioxanes has been condensed with 2-(2-bromoethyl)benzaldehyde to produce chiral dihydroisoquinolinium salts, which are effective asymmetric catalysts for the epoxidation of simple alkenes, giving ees of up to 71 %. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Tandem radical and non-radical reactions mediated with thiols - A new method of cleavage of allylic amines

Thiyl radical promotes the isomerisation of allylic amines into enamines via two consecutive hydrogen atom abstraction steps, and the subsequent polar addition of the corresponding thiol to the enamine results in the cleavage of the C-N bond via a thioaminal intermediate: this reaction provides a mild, metal-free methodology for the deprotection of allylated primary and secondary amines.

AN IMPROVED SYNTHESIS OF (4S,5S)-2,2-DIMETHYL-4-PHENYL-1,3-DIOXAN-5-AMINE

The title compound is prepared in 78percent yield using an improved one-pot procedure which does not require final purification.