198625-17-1

Basic information

• Product Name: (2R,3R)- 3-hydroxy-2-PyrrolidineMethanol
• Synonyms: (2R,3R)- 3-hydroxy-2-PyrrolidineMethanol
• CAS NO: 198625-17-1
• Molecular Formula: C₅H₁₁NO₂
• Molecular Weight: 117.14634
• EINECS: -0
• Mol File: 198625-17-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R,3R)- 3-hydroxy-2-PyrrolidineMethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)- 3-hydroxy-2-PyrrolidineMethanol(198625-17-1)
• EPA Substance Registry System: (2R,3R)- 3-hydroxy-2-PyrrolidineMethanol(198625-17-1)

Safety Data

• Hazardous Substances Data: 198625-17-1(Hazardous Substances Data)

Usage

General Description

(2R,3R)-3-hydroxy-2-pyrrolidinemethanol is a chemical compound with a molecular formula C5H11NO2. It is a derivative of the amino acid proline and is commonly used as a chiral auxiliary in organic synthesis. The (2R,3R) designation indicates the stereochemistry of the molecule, with the two carbon atoms bearing hydroxyl and methyl groups having specific three-dimensional orientations. The pyrrolidine ring structure gives the compound its unique properties, including the ability to act as a chiral catalyst in asymmetric synthesis reactions. Its hydroxy and methyl groups make it a versatile building block in the production of pharmaceuticals and other fine chemicals. The compound is an important intermediate in the synthesis of biologically active compounds and is used in the development of new drugs and materials.

Upstream product

• 98944-20-8 (1R,3R,7R,8S)-9-<(benzyloxy)carbonyl>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.0^3,7>undecane 
• 133161-12-3 (2R,3R)-1-(Benzyloxycarbonyl)-3-hydroxy-2-(hydroxymethyl)pyrrolidine 
• 107690-61-9 3,6-epimino-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 1290130-76-5 C₁₄H₁₅NO₅ 
• 123076-59-5 (3R)-3-hydroxy-N-<(S)-1-phenylethyl>pent-4-enethioamide 
• 123076-61-9 (4R,5R)-N-<(S)-1-phenylethyl>-5-(acetoxymethyl)-4-hydroxypyrrolidin-2-one 
• 123076-60-8 (4R,5S)-N-<(S)-1-phenylethyl>-4-hydroxy-5-(iodomethyl)pyrrolidin-2-one 
• 350592-94-8 (R,R)-3-(4,5-dihydro-2-phenyl-4-oxazolyl)-3-acetoxy-1-propanol 
• 350592-93-7 (R,R)-4-hydroxy-4-(4,5-dihydro-2-phenyl-4-oxazolyl)-1-butene acetate 
• 350592-79-9 (R,R)-4-hydroxy-4-(4,5-dihydro-2-phenyl-4-oxazolyl)-1-butene 
• 350592-96-0 (R,R)-3-acetoxy-2-hydroxymethylpyrrolidine benzoate 
• 123098-96-4 (2R,3R)-2-Hydroxymethyl-1-((S)-1-phenyl-ethyl)-pyrrolidin-3-ol 

Downstream Products

• 121686-90-6 (2R,3R)-N-benzyl-2-(hydroxymethyl)-3-hydroxypyrrolidine 
• 198625-10-4 N-[9-(2-{(2R,3R)-3-Hydroxy-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-9H-purin-6-yl]-benzamide 
• 198625-05-7 N-{9-[2-((2R,3R)-3-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-2-oxo-ethyl]-9H-purin-6-yl}-benzamide 
• 123076-62-0 (2R,3R)-N-benzoyl-2-<(benzoyloxy)methyl>-3-(benzoyloxy)pyrrolidine 

Relevant articles and documents

D-Glucose based syntheses of β-hydroxy derivatives of l-glutamic acid, l-glutamine, l-proline and a dihydroxy pyrrolidine alkaloid

The β-hydroxy derivatives of l-glutamic acid, l-glutamine and l-proline, useful for peptide/protein studies, were synthesized starting from d-glucose. The C2 carbon in d-glucose provided the carboxylic acid functionality, while the amino and β-hydroxy groups of the amino acids were amenable from the C3 and C4 hydroxy groups of the sugar, respectively. The key intermediate with appropriate carbon framework of the target molecules was constructed by homologation of a suitable azido-d-glucofuranose derivative using the Arndt-Eistert reaction. This journal is

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.