858366-85-5

Basic information

• Product Name: (2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol
• Synonyms: (2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol
• CAS NO: 858366-85-5
• Molecular Weight: 208.301
• Mol File: 858366-85-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol(858366-85-5)
• EPA Substance Registry System: (2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol(858366-85-5)

Safety Data

• Hazardous Substances Data: 858366-85-5(Hazardous Substances Data)

Upstream product

• 56577-28-7 methyl (2S,3S)-2-hydroxy-3-methylpentanoate 
• 488-15-3 (2S,3S)-2-Hydroxy-3-methylpentanoic acid 
• 73-32-5 L-isoleucine 
• 858366-75-3 methyl (2S,3S)-2-(benzyloxy)-3-methylpentanoate 

Downstream Products

• 858366-80-0 (2S,3S)-2-(benzyloxy)-3-methylpentanal 
• 858366-96-8 {[(E,3S,4S)-4-methyl-1-nitrohex-1-en-3-yloxy]methyl}benzene 
• 858366-90-2 (3S,4S)-3-Benzyloxy-4-methyl-1-nitro-hexan-2-ol 
• 858367-21-2 (2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester 
• 858367-10-9 (2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-5-cyclopropyl-4-nitropyrrolidine-2-carboxylic acid 
• 858367-17-6 (2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-4-nitro-5-phenylpyrrolidine 
• 858367-23-4 (2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine 
• 858367-06-3 (2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-4-nitro-5-phenylpyrrolidine-2-carboxylic acid 
• 858367-12-1 (2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylpyrrolidine-2-carboxylic acid 
• 858367-08-5 (2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-5-cyclohexyl-4-nitropyrrolidine-2-carboxylic acid 
• 858367-19-8 (2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclohexyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester 
• 868526-29-8 {[(2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester 
• 862666-28-2 {[(2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester 
• 868526-30-1 {[(2S,3S,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-2-methyl-4-nitro-5-phenyl-pyrrolidine-2-carbonyl]-amino}-acetic acid methyl ester 

Relevant articles and documents

Design, synthesis, and functional evaluation of leukocyte function associated antigen-1 antagonists in early and late stages of cancer development

The integrin leukocyte function associated antigen 1 (LFA-1) binds the intercellular adhesion molecule 1 (ICAM-1) by its αL-chain inserted domain (I-domain). This interaction plays a key role in cancer and other diseases. We report the structure-based design, small-scale synthesis, and biological activity evaluation of a novel family of LFA-1 antagonists. The design led to the synthesis of a family of highly substituted homochiral pyrrolidines with antiproliferative and antimetastatic activity in a murine model of colon carcinoma, as well as potent antiadhesive properties in several cancer cell lines in the low micromolar range. NMR analysis of their binding to the isolated I-domain shows that they bind to the I-domain allosteric site (IDAS), the binding site of other allosteric LFA-1 inhibitors. These results provide evidence of the potential therapeutic value of a new set of LFA-1 inhibitors, whose further development is facilitated by a synthetic strategy that is versatile and fully stereocontrolled.