198625-17-1

Usage

Uses

Used in Organic Synthesis:
(2R,3R)-3-hydroxy-2-pyrrolidinemethanol is used as a chiral auxiliary for enhancing the selectivity and efficiency of asymmetric synthesis reactions. Its unique stereochemistry and pyrrolidine ring structure contribute to its effectiveness in this application.
Used in Pharmaceutical Production:
As a building block, (2R,3R)-3-hydroxy-2-pyrrolidinemethanol is utilized in the synthesis of various biologically active compounds and pharmaceuticals. Its hydroxy and methyl groups provide versatility in the development of new drugs and materials.
Used in Chiral Catalyst Development:
(2R,3R)-3-hydroxy-2-pyrrolidinemethanol is employed as a chiral catalyst in asymmetric synthesis reactions, enabling the production of enantiomerically pure compounds, which are essential in the pharmaceutical and chemical industries.
Used in Research and Development:
(2R,3R)3-hydroxy-2-PyrrolidineMethanol serves as an important intermediate in the synthesis of biologically active compounds, making it a valuable tool for researchers in the development of new drugs and materials across various industries.

Upstream product

• 123098-96-4 (2R,3R)-2-Hydroxymethyl-1-((S)-1-phenyl-ethyl)-pyrrolidin-3-ol 
• 1290130-76-5 C₁₄H₁₅NO₅ 
• 107690-61-9 3,6-epimino-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 133161-12-3 (2R,3R)-1-(Benzyloxycarbonyl)-3-hydroxy-2-(hydroxymethyl)pyrrolidine 
• 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 
• 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 

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 academic research and scientific papers

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.

Electrophilic Olefin Heterocyclization in Organic Synthesis. Stereoselective Synthesis of 4,5-Disubstituted γ-Lactams by Iodine-Induced Lactam Formation of γ,δ-Unsaturated Thioimidates

Iodine-induced lactamization of γ,δ-unsaturated thioimidates proceeds regioselectively to provide γ-lactams.The iodolactamization with allylic substituents brings about 1,2-asymmetric induction, which depends on the allyl groups.Transformation of the cis-4-hydroxy-5-(iodomethyl)pyrrolidin-2-one (24a) among these highly functionalized γ-lactams into several biologically active compounds is described.In addition, the conversion of an optically active form of 24a is discussed.