381718-65-6

Basic information

• Product Name: 4(S)-(benzoylamino)-1,2-(R and S)-pentanediol
• Synonyms: 4(S)-(benzoylamino)-1,2-(R and S)-pentanediol
• CAS NO: 381718-65-6
• Molecular Weight: 223.272
• Mol File: 381718-65-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4(S)-(benzoylamino)-1,2-(R and S)-pentanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 4(S)-(benzoylamino)-1,2-(R and S)-pentanediol(381718-65-6)
• EPA Substance Registry System: 4(S)-(benzoylamino)-1,2-(R and S)-pentanediol(381718-65-6)

Safety Data

• Hazardous Substances Data: 381718-65-6(Hazardous Substances Data)

Upstream product

• 381718-59-8 (S)-3-(benzoylamino)-4-pentene 
• 113034-32-5 methyl ester of (S)-3-(benzoylamino)butanoic acid 
• 98-88-4 benzoyl chloride 
• 74720-10-8 (S)-3-(benzoylamino)butyraldehyde 
• 74720-06-2 (S)-3-(benzoylamino)butanoic acid 

Downstream Products

• 65-85-0 benzoic acid 
• 381718-60-1 4(S)-amino-1,2-(R and S)-pentanediol 

Relevant articles and documents

Stereospecific synthesis of oligonucleotides containing crotonaldehyde adducts of deoxyguanosine

Crotonaldehyde reacts with DNA to form two diastereomeric 1,N2 cyclic adducts of deoxyguanosine. A synthesis of the two diastereomeric deoxynucleosides has been achieved by reaction of mixed diastereomers of 4-amino-1,2-pentanediol with 2-fluoro-O6-(trimethylsilylethyl)-deoxyinosine. The resulting N2-(1-methyl-3,4-dihydroxybutyl)-deoxyguanosine was treated with NaIO4, cleaving the vicinal diol to the aldehyde. Spontaneous cyclization gave the two diastereomers of the crotonaldehyde-adducted nucleoside that were readily separated by HPLC. The absolute configurations were assigned by an enantiospecific synthesis of one diastereomer from (S)-3-aminobutanoic acid. The synthetic strategy has been extended to preparation of a site-specifically adducted oligonucleotide by reaction of the mixed diastereomers of 4-amino-1,2-pentanediol with an 8-mer oligonucleotide containing 2-fluoro-O6-(trimethylsilylethyl)-deoxyinosine. The diastereomeric oligonucleotides were separated by HPLC and absolute configurations of the adducts were established by enzymatic digestion to the adducted nucleosides.