167938-56-9

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-(S)-1-AMINO-2-PROPANOL is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its chiral nature and clear, colorless liquid form make it a valuable component in the development of enantiomerically pure compounds, which are crucial for the efficacy and safety of many pharmaceutical products.
As a pharmaceutical intermediate, N-BOC-(S)-1-AMINO-2-PROPANOL plays a critical role in the synthesis of various drug molecules, contributing to the advancement of medical treatments and therapies. Its unique chemical properties allow for targeted drug development, ensuring that the final products are both effective and safe for use in various medical applications.

InChI:InChI=1/C8H17NO3/c1-6(10)5-9-7(11)12-8(2,3)4/h6,10H,5H2,1-4H3,(H,9,11)/t6-/m0/s1

Upstream product

• 123-20-6 vinyl n-butyrate 
• 95656-86-3 tert-butyl 2-hydroxypropylcarbamate 
• 4248-19-5 tert-butyl carbazate 
• 75-56-9 methyloxirane 

Downstream Products

• 352303-74-3 3-[2-N-Boc-amino-1-(R)-methylethyl]-5-bromo-1-(2,6-difluorobenzyl)-6-methyluracil 
• 16066-84-5 N-(tert-butoxycarbonyl)methylamine 
• 1443216-71-4 C₂₇H₃₅N₅O₆ 
• 1452925-35-7 C₁₅H₂₂INO₄ 
• 1399008-14-0 di-tert-butyl ((2S,2'S)-((2-iodo-1,3-phenylene)bis(oxy))bis(propane-2,1-diyl))dicarbamate 
• 907546-01-4 tert-butyl N-[(2S)-2-methoxypropyl]carbamate 
• 1338090-92-8 [(S)-2-(3-trifluoromethylphenyl)propyl]carbamic acid tert-butyl ester 
• 396074-50-3 (S)-5-methyl-2,2-dioxo[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester 
• 675606-03-8 3-[2-N-Boc-amino-1-(R)-methylethyl]-1-(2,6-difluorobenzyl)-5-(2-fluoro-3-methoxyphenyl)-6-methyluracil 
• 181369-36-8 tert-butyl (S)-3-methyl-2H-azirine-2-carboxylate 
• 937375-79-6 (+)-tert-butyl (2S,3R)-3-methylaziridine-2-carboxylate 
• 129319-91-1 (R)-(-)-N-(tert-Butoxycarbonyl)-2-methylaziridine 

Relevant academic research and scientific papers

Asymmetric catalytic synthesis of enantiopure N-protected 1,2-amino alcohols

(Chemical Equation Presented) The asymmetric aminolytic kinetic resolution (AKR) of racemic terminal epoxides using carbamates as the nucleophile catalyzed by (salen)CoIII complex provides a practical and straightforward method for the synthesis of both aliphatic and aromatic N-Boc- or N-Cbz-protected 1,2-amino alcohols in almost enantiomerically pure form (ee ≥ 99%). The AKR uses an easily accessible catalyst and inexpensive starting materials, and the reactions are conveniently carried out at room temperature under an air atmosphere.

Hydrogen-Bonding-Driven Enantioselective Resolution against the Kazlauskas Rule To Afford γ-Amino Alcohols by Candida rugosa Lipase

Most lipases resolve secondary alcohols in accordance with the Kazlauskas rule to give the R enantiomers. In a similar manner to other lipases, Candida rugosa lipase (CRL) exhibits R enantioselectivity towards heptan-2-ol, although the enantiomeric ratio (E) is low (E=1.6). However, unexpected enantioselectivity (i.e., S enantioselectivity, E=58) of CRL towards 4-(tertbutoxycarbonylamino)butan-2-ol, which has a similar chain length to heptan-2-ol, has been observed. To develop a deeper understanding of the molecular basis for this unusual enantioselectivity, we have conducted a series of molecular modeling and substrate engineering experiments. The results of these computational and experimental analyses indicated that a hydrogen bond between the Ser450 residue and the nitrogen atom of the carbamate group is critical to stabilize the transition state of the S enantiomer.