81036-97-7

Basic information

• Product Name: (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one
• Synonyms: (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one
• CAS NO: 81036-97-7
• Molecular Weight: 220.268
• Mol File: 81036-97-7.mol
• Article Data: 25

Chemical Properties

• Melting Point: 138-140 °C(Solv: ethyl acetate (141-78-6); heptane (142-82-5))
• Boiling Point: 331.3±30.0 °C(Predicted)
• Density: 1.113±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one(81036-97-7)
• EPA Substance Registry System: (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one(81036-97-7)

Safety Data

• Hazardous Substances Data: 81036-97-7(Hazardous Substances Data)

Usage

Description

(2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one is a chiral chemical compound with the molecular formula C13H18O3. It features a cyclic structure composed of a dioxolane ring with two oxygen atoms, and is adorned with a tert-butyl and phenyl group. (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one is recognized for its potential as a chiral building block in the realm of organic synthesis, particularly for the creation of pharmaceuticals and agrochemicals. Additionally, it serves as a chiral ligand for metal-catalyzed asymmetric reactions, with its (2S,5S) configuration providing unique reactivity and selectivity in chemical processes, thus making it an indispensable asset in synthetic chemistry.

Uses

Used in Pharmaceutical Industry:
(2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one is utilized as a chiral building block for the synthesis of various pharmaceuticals. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which is crucial for the development of drugs with specific therapeutic effects and minimal side effects.
Used in Agrochemical Industry:
In the agrochemical sector, (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one is employed as a chiral building block for the synthesis of agrochemicals. (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one's ability to produce enantiomerically pure products ensures the development of effective and targeted agrochemicals with reduced environmental impact.
Used in Asymmetric Catalysis:
(2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one also serves as a chiral ligand in metal-catalyzed asymmetric reactions. Its (2S,5S) configuration imparts specific reactivity and selectivity, facilitating the synthesis of enantiomerically pure compounds with high yields and selectivity, which is vital for the production of complex organic molecules with precise stereochemistry.

Upstream product

• 630-19-3 pivalaldehyde 
• 611-71-2 MANDELIC ACID 
• 62617-39-4 1,1-dimethoxy-2,2-dimethylpropane 
• 78804-02-1 (+/-)-trimethylsilyl 2-<(trimethylsilyl)oxy>-2-phenylethanoate 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 120-92-3 cyclopentanone 
• 17199-29-0 (S)-Mandelic acid 

Downstream Products

• 268216-65-5 cis-(2S,5R)-2-(tert-butyl)-5-phenyl-5-(cyclohexyl-1-ol)-1,3-dioxolan-4-one 
• 654068-39-0 (2S,5R)-2-tert-butyl-5-(3-methyl-4-nitrophenyl)-5-phenyl-1,3-dioxolan-4-one 
• 654068-40-3 (2S,5R)-2-tert-butyl-5-(3-methoxy-4-nitrophenyl)-5-phenyl-1,3-dioxolan-4-one 
• 654068-43-6 (2S,5R)-2-tert-butyl-5-(2-chloro-4-nitrophenyl)-5-phenyl-1,3-dioxolan-4-one 
• 81036-99-9 (2S,5S)-5-allyl-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one 
• 1026552-59-9 (2S,5S)-2-tert-Butyl-5-cyclohex-2-enyl-5-phenyl-[1,3]dioxolan-4-one 
• 302842-80-4 (2S,5R)-2-(tert-butyl)-5-phenyl-5-(1-hydroxycyclopentyl)-1,3-dioxolan-4-one 
• 81037-00-5 (S)-2-tert-Butyl-5-phenyl-5-propyl-[1,3]dioxolan-4-one 
• 81036-99-9 (S)-5-Allyl-2-tert-butyl-5-phenyl-[1,3]dioxolan-4-one 
• 195388-29-5 (3R,4S)-3-hydroxy-1,3,4-triphenylazetidin-2-one 
• 195388-30-8 (3R,4R)-3-Hydroxy-1,3,4-triphenyl-azetidin-2-one 

Relevant articles and documents

Practical and robust method for the preparation of Seebach and Frater's chiral template, cis-2-substituted 5-methyl(or phenyl)-1,3-dioxolan-4-ones

A practical and highly stereoselective method for the preparation of three cis-2-substituted 5-methyl (orphenyl)-1,3-dioxolan-4-ones 3a and 7a (Seebach and Frater's chiral template), and a new modified analogue 7b has been developed. The present robust me

Discovery of a Novel Muscarinic Receptor PET Radioligand with Rapid Kinetics in the Monkey Brain

Positron emission tomography (PET), together with a suitable radioligand, is one of the more prominent methods for measuring changes in synaptic neurotransmitter concentrations in vivo. The radioligand of choice for such measurements on the cholinergic sy

An efficient synthetic approach towards fully functionalized tetronic acids: The use of 1,3-dioxolane-2,4-diones as novel protected-activated synthons of α-hydroxy acids

A new strategy for the synthesis of tetronic acids with control over the regioselective introduction of substituents at the C-5 position has been developed. The construction of the densely functionalized quaternary carbon center within these molecules is of great importance. The key element for the proposed protocol was the utilization of O-carboxyanhydrides (OCA's) of optically active α-hydroxy acids, as promising bidentate protective/activating precursors. The structure of the new compounds was investigated by using NMR spectral data and X-ray structural analyses.