942308-58-9

Basic information

• Product Name: （2s，4s）-benzyl-4-hydroxy-2-（hydroxymethyl）pyrrolidine..
• Synonyms: （2s，4s）-benzyl-4-hydroxy-2-（hydroxymethyl）pyrrolidine..;(2S,4S)-4-hydroxy-2-(hydroxymethyl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester;(2S,4R)-benzyl-4-hydroxy-2-(hydroxymethyl)pyrrolidine;(2S,4S)-benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS NO: 942308-58-9
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 207.271
• Mol File: 942308-58-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 433.897 °C at 760 mmHg
• Flash Point: 216.214 °C
• Appearance: /
• Density: 1.298 g/cm³
• Refractive Index: 1.595
• Storage Temp.: 2-8°C
• CAS DataBase Reference: （2s，4s）-benzyl-4-hydroxy-2-（hydroxymethyl）pyrrolidine..(CAS DataBase Reference)
• NIST Chemistry Reference: （2s，4s）-benzyl-4-hydroxy-2-（hydroxymethyl）pyrrolidine..(942308-58-9)
• EPA Substance Registry System: （2s，4s）-benzyl-4-hydroxy-2-（hydroxymethyl）pyrrolidine..(942308-58-9)

Safety Data

• Hazardous Substances Data: 942308-58-9(Hazardous Substances Data)

Usage

General Description

(2s,4s)-benzyl-4-hydroxy-2-(hydroxymethyl)pyrrolidine is a chemical compound with the molecular formula C15H23NO2. It is a pyrrolidine derivative with a benzyl group and a hydroxy group attached to the pyrrolidine ring. （2s，4s）-benzyl-4-hydroxy-2-（hydroxymethyl）pyrrolidine.. is used in organic synthesis and medicinal chemistry, and it has potential applications in drug development and pharmaceutical research. The benzyl group and hydroxy group contribute to the compound's reactivity and potential biological activity, making it a valuable building block in the synthesis of pharmaceutical compounds and other organic molecules.

InChI:InChI=1/C12H17NO2/c14-9-11-6-12(15)8-13(11)7-10-4-2-1-3-5-10/h1-5,11-12,14-15H,6-9H2/t11-,12-/m0/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 1365659-16-0 (1S,4S)-N-Cbz-6-(R/S)-hydroxy-5-oxa-2-aza-bicyclo[2.2.1]heptane 
• 1365659-15-9 (1S,4S)-N-Cbz-6-(R/S)-methoxy-5-oxa-2-aza-bicyclo[2.2.1]heptane 
• 1365659-14-8 (1S,4S)-3-(R/S)-methoxy-2-oxa-5-aza-bicyclo[2.2.1]heptane 
• 618-27-9 hydroxy L-proline 
• 16217-15-5 1-benzyloxycarbonyl-4-oxo-L-proline methyl ester 
• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 57653-35-7 (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-methyl 

Downstream Products

• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 618-27-9 hydroxy L-proline 
• 153093-07-3 C₁₃H₁₅NO₄ 
• 942308-59-0 1-benzyloxycarbonyl-(2S)-methoxymethyl-(4S)-methoxypyrrolidine 
• 197079-39-3 (S)-benzyl 2-(tert-butyldimethylsilyloxy)methyl-4-oxo-pyrrolidine-1-carboxylate 

Relevant articles and documents

Synthesis of (2S,4S)-4-hydroxyproline from D-glucose

Diacetone-D-glucose 1 gives 3-O-methylxanthate 2 on reaction with NaH=Me I. Reductive deoxygenation of compound 2 by Bu3SnH gives the corresponding 3-deoxy glucose derivative 3 and on acid-catalyzed regioselective deprotection of C-5,6-acetonide gives the diol 4. The diol on oxidative cleavage with NaIO4 gives the aldehyde 5, which on further condensation with benzylamine followed by reduction with NaBH4 gives the amine 7. Z-Protection of the amine followed by methanolysis gives methyl furanoside 9. Reaction of 9 with methanesulfonyl chloride=Et3N gives the corresponding C-3-O-mesylate derivative 10. Catalytic hydrogenation of compound 10 (Pd=C=H2=MeOH 3 kg) gives bicyclic oxaazo compound 11, due to deprotection of the N-benzyl- and Z-protecting groups and intramolecular nucleophilic displacement of the C-2-O-mesylate by the C-5 amine in a one-pot reaction. Z-Protection of the amine 11 followed by acid-catalyzed hydrolysis gives acetal 13. Reduction of acetal by use of NaBH4 gives Z-prolinol 14. Selective oxidation of diol 14 by (2,2,6,6-tetramethylpiperidin-1-yl)-oxyl (TEMPO)=[(bis)(acetoxy)iodo]-benzene (BAIB) and NaClO2=NaH 2PO4, followed by Z-deprotection, gives the title compound I in 3.5% overall yield from D-glucose. Copyright Taylor & Francis Group, LLC.

Carboxy mediated stereoselective reduction of ketones with sodium triacetoxyborohydride: Synthesis of novel 3,4-fused tetrahydropyran and tetrahydrofuran prolines

In the presence of a carboxyl group positioned for participation, NaBH(OAc)3 will reduce the usually unreactive ketones in a stereoselective manner. This reaction was applied in a key step to prepare precursors 7 and 15 toward the title compounds 1 and 2. These results are consistent with the exchange of one of the acetoxy groups in the reducing agent with the carboxy group followed by intramolecular delivery of the hydride.

Nucleosides and Oligonucleotides Derived from trans-4-Hydroxy-N-acetylprolinol

The 4-O-phosphoramidites of monomethoxytritylated 4-hydroxy-N-6-benzoyladenin-9-yl)acetyl>prolinol and 4-hydroxy-N-prolinol were prepared for incorporation into nucleic acids.The L-trans all-adenine oligonucleotide (ON) hybridises to natural oligothymidylate, apparently via triplex formation.All-purine sequences of the L-trans form can also form homo-complexes with their pyrimidine counterpart.The D-trans compounds give larger destabilisation when inserted in DNA.D-trans all-adenine ONs do not form complexes with natural oligothymidylate.For this series of modified ONs no hybridisation could be detected between complementary strands of opposite enantiomeric form.