61739-41-1

Basic information

• Product Name: (4R)-2-chloro-3,4r-dimethyl-5c-phenyl-[1,3,2]oxazaphospholidine
• CAS NO: 61739-41-1
• Molecular Weight: 229.646
• Mol File: 61739-41-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (4R)-2-chloro-3,4r-dimethyl-5c-phenyl-[1,3,2]oxazaphospholidine(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-2-chloro-3,4r-dimethyl-5c-phenyl-[1,3,2]oxazaphospholidine(61739-41-1)
• EPA Substance Registry System: (4R)-2-chloro-3,4r-dimethyl-5c-phenyl-[1,3,2]oxazaphospholidine(61739-41-1)

Safety Data

• Hazardous Substances Data: 61739-41-1(Hazardous Substances Data)

Upstream product

• 50-98-6 ephedrine hydrochloride 
• 90-81-3 (S,S)-(+)-pseudoephedrine 
• 299-42-3 ephedrine 
• 67069-59-4 N-methyl-[(1S,2R)-(2-phenyl-1-methyl-2-trimethylsilyloxy)]ethylamine 
• 299-42-3 (R,R)-(-)-pseudoephedrine 

Downstream Products

• 32018-63-6 dimethylamino-2 dimethyl-3,4 phenyl-5 oxazaphospholane-1,3,2 
• 155730-44-2 (2S,4S,5R)-2-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-3,4-dimethyl-5-phenyl-[1,3,2]oxazaphospholidine 
• 53648-94-5 trans-2-methoxy-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholane 
• 53648-94-5 cis-2-methoxy-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholane 
• 89878-06-8 2-ethoxy-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine 
• 146601-32-3 (4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethyl-5-phenyl-[1,3,2]oxazaphospholidine 
• 146601-33-4 (4S,5R)-3,4-Dimethyl-5-phenyl-2-triethylsilanyloxy-[1,3,2]oxazaphospholidine 
• 149650-19-1 (2R,4S,5R)-2-(2-Methoxyphenyl)-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine 
• 146601-29-8 <(1R,2S)-O,N-ephedrine>P(=O)H 
• 146601-31-2 (4S,5R)-3,4-Dimethyl-5-phenyl-2-triphenylsilanyloxy-[1,3,2]oxazaphospholidine 
• 149650-18-0 (2R,4S,5R)-2-(2-Methoxyphenyl)-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine 2-oxide 
• 130818-07-4 (S_P)-(-)-N-<(1S,2R)-2-Hydroxy-1-methyl-2-phenylethyl>-N-methyl-P-(2-methoxyphenyl)-P-phenylphosphinamide 

Relevant articles and documents

Enantiodivergent synthesis of P-chirogenic phosphines

Several approaches for the enantiodivergent synthesis of P-chirogenic mono- and diphosphines are described, using ephedrine methodology and phosphine borane chemistry. Firstly, both enantiomers of a tertiary phosphine can be obtained starting from the same oxazaphospholidine borane complex, prepared from (+)-ephedrine, when changing the order of addition of the organolithium reagents during the synthetic pathway. The second approach is based on the chlorophosphine boranes, which react with an organolithium reagent, to afford the corresponding phosphines with inversion of configuration. In the case where the chlorophosphine borane reacts with the t-butyl lithium reagent, a metal-halogen exchange occurs to afford the corresponding phosphide borane with retention of the configuration. The reaction of the phosphide borane with an alkyl halide leads to the same phosphine, but with the opposite configuration. Another approach depends on the diastereoselective preparation of the starting oxazaphospholidine borane complex from (-)-ephedrine, which leads according the case, to either one or the other enantiomer of a phosphine. Finally, the synthesis of (R,R)- and (S,S)-1,2-bis(methylphenylphosphino)ethane is also demonstrated using both enantiomers of the P-chirogenic diphosphinite diborane, which simultaneously allows the introduction of alkyl- or aryl substituents on the phosphorus atoms. In summary, these approaches show the great efficiency of the "ephedrine methodology" for the enantiodivergent synthesis of P-chirogenic mono- and diphosphines, and bearing alkyl or aryl substituents.

Oxazaphospholidine-oxide as an efficient ortho-directing group for the diastereoselective deprotonation of ferrocene

Ortho-lithiation of (2R,4S,5R)-3,4-dimethyl-2-ferrocenyl-5-phenyl[1,3,2] oxazaphospholidine 2-oxide 2 was carried out with diastereoselectivity of >99%, affording a new and efficient way for introducing planar chirality into the ferrocene backbone. Various electrophiles were used to quench the lithiated species, showing the wide applicability of the new ortho-directing group and its potential to generate ligands for use in asymmetric catalysis.

Synthons for oligonucleotide synthesis

The invention provides new reagents and processes for synthesizing oligonucleotides, including stereoselective oligonucleotide synthesis. In a first aspect, the invention provides novel monomer synthons for the synthesis of oligonucleotides. Monomer synthons according to this aspect of the invention are useful in the synthesis of oligonucleotides and can be used in place of the well known beta-cyanoethyl phosphoramidite monomer synthon in the phosphoramidite synthesis procedure. Certain monomer synthons according to this aspect of the invention are useful in this procedure for producing oligonucleotides having defined stereochemistry. In a second aspect, the invention provides processes for synthesizing monomer synthons according to the invention, including diastereomerically enriched or purified monomer synthons. In the processes according to this aspect of the invention, the chemical reactions are stereoretentive so that the products of each reaction retain the same stereoconfiguration as their precursor reagent. In a third aspect, the invention provides processes for synthesizing oligonucleotides using the well known phosphoramidite approach. In the processes according to this aspect of the invention, any of the monomer synthons according to the invention is used in place of the conventional beta-cyanoethyl phosphoramidite.