3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(4-hydroxyphenyl)-, (2S,3S,4S,5S)- (9CI)

Base Information

• Chemical Name: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(4-hydroxyphenyl)-, (2S,3S,4S,5S)- (9CI)
• CAS No.: 431981-75-8
• Molecular Formula: C11H15NO4
• Molecular Weight: 225.24
• Mol file: 431981-75-8.mol

Synonyms:

Chemical Property of 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(4-hydroxyphenyl)-, (2S,3S,4S,5S)- (9CI)

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(4-hydroxyphenyl)-, (2S,3S,4S,5S)- (9CI)

There total 81 articles about 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(4-hydroxyphenyl)-, (2S,3S,4S,5S)- (9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(2R,3R,4R,5R)-3,4-dihydroxy-2-(hydroxymethyl)-5-(4-hydroxyphenyl)pyrrolidine hydrochloride → (2R,3R,4R,5R)-4-(hydroxy)-2-(hydroxymethyl)-5-(4-hydroxyphenyl)pyrrolidin-3-ol (188744-98-1,431981-75-8)

Guidance literature:

With ammonium hydroxide;

DOI:10.1055/s-2007-991059

Reference yield: 96.0%

(2S,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate (1615251-24-5) → (2S,3R,4R,5S)-2-(hydroxymethyl)-5-(4-hydroxyphenyl)-pyrrolidine-3,4-diol (1615251-28-9,188744-98-1,431981-75-8)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c4ob00503a

Reference yield: 93.0%

(2S,3S,4S,5S)-2-benzyloxymethyl-3,4-dibenzyloxy-5-(4-benzyloxyphenyl)-N-hydroxy-pyrrolidine (904893-28-3) → (2S,3S,4S,5S)-2-hydroxymethyl-3,4-dihydroxy-5-(4-hydroxyphenyl)-pyrrolidine (905286-72-8,188744-98-1,431981-75-8)

Guidance literature:

With hydrogen; acetyl chloride; palladium on activated charcoal; In methanol; dichloromethane; for 20h; under 760 Torr;

DOI:10.1021/ol0609210

upstream raw materials:

(3aR,4R,6S,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[4-(tert-butyl-diphenyl-silanyloxy)-phenyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

(3aR,4R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-chloro-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole

Refernces

Stereoselective synthesis of (+)-radicamine B

10.1016/j.tetlet.2011.07.035

The research presents a stereoselective synthesis of the naturally occurring pyrrolidine alkaloid, (+)-radicamine B, which possesses significant biological properties. The synthesis involves 13 steps, starting from commercially available p-hydroxybenzaldehyde, with an overall yield of 9.75%. Key reactions include Sharpless asymmetric epoxidation and Horner–Wadsworth–Emmons (HWE) olefination. Reactants used throughout the synthesis include p-hydroxybenzaldehyde, tosyl chloride, (+)-DET, NaN3, PPh3, Boc anhydride, benzaldehyde dimethylacetal, DIBAL-H, IBX, (OEt)2PO(CH2COOEt), and (+)-DIPT, among others. Analytical techniques employed to characterize the intermediates and final product included 1H NMR, 13C NMR, Mass spectrometry, and IR spectroscopy, with enantioselectivity determined by chiral HPLC. The study also discusses the biological significance of radicamine B and the challenges in its asymmetric synthesis, highlighting the efficiency and linearity of their developed synthetic protocol.

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