431981-75-8

Basic information

• Product Name: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(4-hydroxyphenyl)-, (2S,3S,4S,5S)- (9CI)
• Synonyms: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(4-hydroxyphenyl)-, (2S,3S,4S,5S)- (9CI)
• CAS NO: 431981-75-8
• Molecular Formula: C11H15NO4
• Molecular Weight: 225.2411
• Product Categories: ALCOHOL
• Mol File: 431981-75-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(4-hydroxyphenyl)-, (2S,3S,4S,5S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(4-hydroxyphenyl)-, (2S,3S,4S,5S)- (9CI)(431981-75-8)
• EPA Substance Registry System: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-(4-hydroxyphenyl)-, (2S,3S,4S,5S)- (9CI)(431981-75-8)

Safety Data

• Hazardous Substances Data: 431981-75-8(Hazardous Substances Data)

Upstream product

• 120186-59-6 (4-(benzyloxy)phenyl)magnesium bromide 
• 155931-84-3 (2S,3R,4R)-2,3,5-tri-O-benzyl-4-O-formyl-pentanal 
• 1615251-24-5 (2S,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate 
• 1346680-20-3 (2S,3R,4R,5R)-benzyl 2-(4-(benzyloxy)phenyl)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 1063685-03-9 tert-butyl (4R)-4-[(1R,2S)-1,2-bis(benzyloxy)-3-(4-benzyloxyphenyl)-3-oxopropyl]-2,2-dimethyloxazolidine-3-carboxylate 
• 158349-27-0 (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one 
• 944543-97-9 C₃₄H₃₅NO₆ 
• 944544-00-7 (3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one 
• 944543-93-5 (3S,4R,5R)-5-benzyloxymethyl-3,4-dibenzyloxy-1-(4-methoxybenzyl)-pyrrolidin-2-one 
• 944544-10-9 (2R,3R,4R,5S)-2-(benzyloxymethyl)-5-(4-benzyloxyphenyl)-3,4-dibenzyloxy-pyrrolidine 

Relevant articles and documents

Synthesis of di- and trihydroxy proline derivatives from D-glycals: Application in the synthesis of polysubstituted pyrrolizidines and bioactive 1C-aryl/alkyl pyrrolidines

Six different types of O-benzyl protected proline derivatives have been synthesized from D-glycals and 2C-formyl-glycals. One of the di-O-benzyl protected proline derivatives has been utilized for the synthesis of polysubstituted pyrrolizidines via [3 + 2

Stereoselective total synthesis of (+)-radicamine B via anti,syn,syn-oxazine

The stereoselective total synthesis of (+)-radicamine B was achieved using commercially available D-4-hydroxy-phenylglycine via chiral 1,3-oxazine, which has been applied to synthesis of amino polyols such as DAB-1, D-fagomine, and phytosphingosines. The key steps in this strategy were the palladium(0)-catalyzed stereoselective intramolecular oxazine formation, an extension of the chirality of anti,syn-oxazine with Lewis acid and vinylmagnesium bromide, and pyrrolidine ring formation via hydrogenation reaction. The chiral extension is also applicable to other chiral 1,3-oxazine derived from D-4-hydroxy-phenylglycine.

Sugar-derived cyclic imines: One-pot synthesis and direct functionalization

A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines.

An easy route to synthetic analogues of radicamine B, codonopsine and codonopsinine from d-mannitol

A general strategy for the synthesis of analogues of radicamine B has been carried out from d-mannitol. This method has been further extended to the synthesis of analogues of codonopsine and codonopsinine using appropriate Grignard reagents. The hence obtained molecules have been tested against various commercially available glycosidases and found to act as moderate to good inhibitors. This journal is the Partner Organisations 2014.

Total synthesis of radicamine B and 5-epi-radicamine B

Radicamine B 5 was synthesized from p-hydroxy benzaldehyde 7 stereoselectively using acid catalysed amido cyclisation with the help of neighbouring group participation (NGP). Without NGP both radicamine B 5 and its epimer 5-epi radicamine B 6 were obtaine

Stereoselective synthesis of (+)-radicamine B

A simple and efficient stereoselective synthesis of naturally occurring pyrrolidine alkaloid, radicamine B has been accomplished in 13 steps from the commercially available starting materials with an overall yield of 9.75%. The synthesis utilizes Sharples

Total synthesis of pyrrolidine alkaloid, Radicamine-B via Stille coupling

Total synthesis of (-) Radicamine-B is achieved in eight steps from (R)-(+)-Garner aldehyde in a stereoflexible manner involving Stille coupling and one-pot domino epoxidation-pyrrolidine formation as key steps.

Nucleophilic additions to cyclic nitrones en route to iminocyclitols - Total syntheses of DMDP, 6-deoxy-DMDP, DAB-1, CYB-3, nectrisine, and radicamine B

Highly diastereoselective nucleophilic additions to cyclic nitrones derived from L-malic acid and D-arabinose have been used for the construction of enantiomerically pure polyhydroxylated pyrrolidines. The synthetic strategy adopted was based on an oxidat

Short, stereoselective synthesis of the naturally occurring pyrrolidine radicamine B and a formal synthesis of nectrisine

(Chemical Equation Presented) A short, stereoselective synthesis of the naturally occurring pyrrolidine radicamine B is reported. Garner's (R)-aldehyde, prepared from D-serine, was the chiral starting material. The pyrrolidine ring was stereoselectively created in a very efficient way through a five-step, one-pot transformation. In addition, an intermediate of this synthesis was transformed into an intermediate of a previously published synthesis of the potent α-glucosidase inhibitor nectrisine.

Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library

Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A (20) and B (18) against α-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 μM, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases.