80724-92-1

Usage

Uses

Used in Organic Synthesis:
Lithooxazoline is used as a catalyst for the formation of carbon-carbon and carbon-heteroatom bonds in various organic reactions. Its chiral nature allows for the creation of enantiopure compounds, which is crucial in the synthesis of pharmaceuticals and other specialty chemicals.
Used in Asymmetric Synthesis:
Lithooxazoline is used as a chiral catalyst in asymmetric synthesis, enabling the production of enantiomerically pure compounds. This is particularly important in the pharmaceutical industry, where the stereochemistry of a molecule can significantly impact its biological activity and efficacy.
Used in Polymer Chemistry:
Lithooxazoline derivatives are studied for their potential applications in polymer chemistry, where they can be used to create novel polymers with specific properties, such as improved stability or enhanced reactivity.
Used in Materials Science:
Lithooxazoline compounds are being investigated for their potential use in materials science, where they could contribute to the development of new materials with unique characteristics, such as increased strength or improved thermal properties.

InChI:InChI=1/C28H47NO2/c1-18(6-11-25-29-26(2,3)17-31-25)22-9-10-23-21-8-7-19-16-20(30)12-14-27(19,4)24(21)13-15-28(22,23)5/h18-24,30H,6-17H2,1-5H3/t18-,19-,20-,21+,22-,23+,24+,27+,28-/m1/s1

Upstream product

• 434-13-9 Lithocholic acid 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 80724-89-6 2-(3α-formyloxy-24-nor-5β-cholanyl)-4,4-dimethyl-2-oxazoline 
• 4966-78-3 3α-formyloxy-5β-cholan-24-oic acid chloride 
• 5015-59-8 3α-formyloxy-5β-cholan-24-oic acid 
• 80724-85-2 2-(3α-formyloxy-5β-cholan-24-amido)-2-methyl-1-propanol 

Downstream Products

• 139286-84-3 2'-(3α-Benzyloxy-24-norcholan-23-yl)-2',4',4'-trimethyl-4',5'-dihydrooxazoline-N-hydroxide 
• 139286-82-1 5'-(3α-Benzyloxy-24-norcholan-23-yl)-1'-aza-4',6'-dioxabicyclo<3.1.0>hexane 
• 139286-83-2 2'-(3α-Benzyloxy-24-norcholan-23-yl)-4',4'-dimethyl-4',5'-dihydrooxazoline-N-oxide 
• 139399-78-3 2'-(3α-Benzyloxy-24-norcholan-23-yl)-2',4',4'-trimethyl-4',5'-dihydooxazoline-N-oxide 
• 139286-85-4 2'-(3α-Benzyloxy-5β-norcholan)-propan-2'-ol 
• 134878-46-9 Methyl-3α-benzyloxy-5percentb-cholan-24-oate 
• 139286-86-5 (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-Benzyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 2-methyl-2-nitroso-propyl ester 

Relevant academic research and scientific papers

2′(3α-Benzyloxy-24-norcholan-23-yl)-2′,4′4′- trimethyl-4′,5′-dihydrooxazoline-N-oxyl as a potential spin probe for model membranes

A new steroidal doxyl (4,4-dimethyloxazolidine-N-oxyl) nitroxide (SDN) viz, 2′-(3α-benzyloxy-24-norcholan-2′-yl)-2′, 4′4′-trimethyl-4′,5′-dihydrooxazoline-N-oxyl has been synthetized. This is expected to have higher mobility over other spin labels reported earlier. The localization of this spin probe in lipid bilayers has been determined using 1H NMR and 31P NMR techniques. The alterations induced by drugs in the membrane characteristics such as phase transition and permeability have been investigated using electron paramagnetic resonance (EPR) techniques. The results show the applicability of SDN as a potential spin probe in the study of biomembranes.

SYNTHESIS OF 2'-(3α-BENZYLOXY-24-NORCHOLAN-23-YL)-2',4',4'-TRIMETHYL-4',5'-DIHYDROOXAZOLINE-N-OXYL - A NEW POTENTIAL SPIN PROBE FOR BIOMEMBRANES

The synthesis of a new steroidal nitroxide, viz. 2'-(3α-benzyloxy-24-norcholan-23-yl)-2',4',4'-trimethyl-4',5'-dihydrooxazoline-N-oxyl 7, a potential spin probe for biomembranes is described.The title compound in improved yield could be obtained by a direct Grignard reaction on the oxaziridine 4.This effected a one-step reduction in the overall synthetic sequence.The methodology of the Grignard reaction on the oxaziridine to yield the nitroxide is reported for the first time.In dilute solutions, the isotropic ESR parameters for 7 have been measured.

On the protection of 3α-hydroxy group of A/B cis steroids

The difficulties encountered in the protection of 3α-hydroxy group of lithocholic acid 1 with three different types of protective groups are described. Only benzyl ether derivative was found to be suitable for synthetic transformations. The methodology for the synthesis of benzyl ethers of A/B cis steroids is reported for the first time.

THE PREPARATION OF BILE ACID AMIDES AND OXAZOLINES

Amides obtained by the condensation of some bile acid chlorides with 2-amino-2-methyl-1-propanol on cyclization yield bile acid oxazolines.Physical properties of these bile acid derivatives are described.Some of the oxazolines are non-toxic and are inhibitors of 7-dehydroxylaseactivity in fecal anaerobic bacteria and purified enzymes from these bacteria.