119717-03-2

Basic information

• Product Name: (3R,S,2S)-2-[(phenylsulfonyl)amino]-5-chloro-1,3-dihydroxypentanes
• CAS NO: 119717-03-2
• Molecular Weight: 293.771
• Mol File: 119717-03-2.mol

Chemical Properties

• CAS DataBase Reference: (3R,S,2S)-2-[(phenylsulfonyl)amino]-5-chloro-1,3-dihydroxypentanes(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,S,2S)-2-[(phenylsulfonyl)amino]-5-chloro-1,3-dihydroxypentanes(119717-03-2)
• EPA Substance Registry System: (3R,S,2S)-2-[(phenylsulfonyl)amino]-5-chloro-1,3-dihydroxypentanes(119717-03-2)

Safety Data

• Hazardous Substances Data: 119717-03-2(Hazardous Substances Data)

Upstream product

• 85828-29-1 3-hydroxy-2-[(phenylsulfonyl)amino]propanoic acid 
• 85828-39-3 (S)-4-[(Phenylsulfonyl)amino]-5-hydroxy-3-pentenone 
• 119593-50-9 (2S)-2-[(phenylsulfonyl)amino]-5-chloro-1-hydroxy-3-pentanone 

Downstream Products

• 119593-53-2 (2S,3R)-3-hydroxy-2-(hydroxymethyl)-1-(phenylsulfonyl)pyrrolidine 
• 119593-52-1 (2S,3S)-3-hydroxy-2-(hydroxymethyl)-1-(phenylsulfonyl)pyrrolidine 
• 119593-77-0 (2R,3R)-N-(phenylsulfonyl)-3-hydroxyproline 
• 198625-07-9 3(R)-hydroxy-2(S)-monomethoxytrityloxymethyl-N-[(thymin-1-yl)-acetyl] pyrrolidine 
• 198625-04-6 N-{9-[2-((2S,3R)-3-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-2-oxo-ethyl]-9H-purin-6-yl}-benzamide 
• 198705-78-1 (S,R)-3-hydroxy-2-hydroxymethylpyrrolidine 
• 198625-09-1 N-[9-(2-{(2S,3R)-3-Hydroxy-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-9H-purin-6-yl]-benzamide 
• 350592-84-6 cis-3-hydroxy-D-prolinol 

Relevant articles and documents

Oligonucleotides with 3-hydroxy-N-acetylprolinol as sugar substitute

Fully modified oligonucleotides were synthesised from the 3-O-phosphoramidites of monomethoxytritylated trans-3-hydroxy-N-[(N6-benzoyladenin-9-yl)-acetyl]-prolinol [(2S,3R) and (2R,3S) series], trans-3-hydroxy-N-[(thymin-1-yl)-acetyl]-prolinol [(2S,3R) and (2R,3S) series], and cis-3-hydroxy-N-[(N6-benzoyl-adenin-9-yl)-acetyl]-L-prolinol (2R,3R). Remarkably, as well the L-trans (2R,3S) as the D-trans (2S,3R) all-adenine oligonucleotides are capable of hybridisation with complementary DNA and RNA. With modified all-thymine trans-oligomers no complexation with natural nucleic acids was observed. However, complex formation between two modified strands of the same sense of chirality does occur with formation of a triple stranded complex. The all-thymine oligonucleotides with trans-3-HO-N-acetylprolinol backbone are capable of hybridisation with trans-4-HO-N-acetylprolinol oligoadenylates of the same enantiomeric form in both the D and the L series, and inversely, the all-adenine oligonucleotide with the trans-3-HO conformation hybridises with the trans-4-HO oligothymidylates. While the former interactions have a triple stranded origin, the latter are 1:1 interactions. No interactions were noticed upon mixing oligonucleotide analogues of different sense of chirality. Modified mixed trans-3-HO A,T sequences display no hybridisation with complementary nucleic acids, nor homocomplex formation. The L-cis all-adenine oligonucleotide hybridises with its RNA complement. Several complexes were investigated by circular dichroism and microcalorimetry. In conclusion, the 3-hydroxy-N-acetylprolinol system represents an example of homochiral oligonucleotides built up from two enantiomeric forms and hybridizing both with natural nucleic acids.

Chirospecific Synthesis of β-Hydroxy α-Amino Acids

A variety of β-hydroxy α-amino acids have been synthesized with complete enantiomeric purity from L-serine.These include β-hydroxyglutamic acid, β-hydroxypipecolic acid, β-hydroxylysine, β-hydroxyproline, and β-hydroxymethionine.The syntheses proceed by t