1,3-Oxazine as a chiral building block used in the total synthesis of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine

Park, Seok‐Hwi; Kim, Jiyeon; Kim, Jin-Seok; Jung, Changyoung; Song, Dong‐Keun; Ham, Won‐Hun

doi:10.1016/j.tetasy.2015.05.008

Cited by 24 publications

(17 citation statements)

References 45 publications

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“…Melting points were determined in open glass capillaries and were not corrected. 1 H NMR and 13 C NMR were recorded either in CDCl 3 or D 2 O on a Bruker Avance III 500 MHz spectrometer. Chemical shifts are given using tetramethylsilane (δ TMS = 0 ppm) as an internal standard.…”

Section: Methodsmentioning

confidence: 99%

“…Prepared by the literature procedure: Colourless oil; yield 75 g, 97%; R f = 0.12 (petroleum ether/ethyl acetate 6:1); 1 H NMR (500 MHz, CDCl 3 ) δ 3.45 (s, 3H), 3.70-3.90 (m, 5H), 4.07 (t, J = 8 Hz, 1H), 4.50-4.98 (m, 8H), 5.12 (d, J = 10.9 Hz, 1H), 7.27-7.46 (m, 20H); 13…”

Section: 346-tetra-o-benzyl-α-d-gluco-methyl-pyranoside (2) 26mentioning

confidence: 99%

“…Prepared by the literature procedure: Colourless oil; yield 8.1 g, 82%; R f = 0.21 (petroleum ether/ethyl acetate 2:1); 1 H NMR (500 MHz, CDCl 3 ) δ 2.81 (s, OH), 3.6 (dd, J = 5 Hz, J = 10 Hz, 1H), 3.80 (dd, J = 3, 9 Hz, 1H), 3.83-4.00 (m, 2H), 4.10 (dd, J = 3, 5 Hz, 1H), 4.28 (d, J = 2 Hz, 1H), 4.50-4.70 (m, 8H), 6.00 (s, 1H), 6.67 (s, 1H), 7.20-7.40 (m, 20H); 13…”

Section: 346-tetra-o-benzyl-d-gluconamide (4) 25mentioning

confidence: 99%

“…12 Several routes have been designed and reported for the synthesis of iminosugars due to the promising biological activities of these compounds. 2,11,[13][14][15][16] Most of the reported syntheses of 1-deoxynojirimycin involve the oxidation of the 5-hydroxyl group of a carbohydrate precursor by using pyridine-SO 3 complex/DMSO, 17 Ac 2 O/DMSO, 18,19 DCC/ DMSO 20 and intramolecular cyclisation of resulting ketosugars into gluconolactams via a reductive amination approach using reducing reagents (NaBH 3 CN 10,[21][22][23][24][25] and Et 3 SiH/BF 3 •Et 2 O 17 ) as shown in Fig. 2.…”

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confidence: 99%

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Synthesis of 1-Deoxynojirimycin: Exploration of Optimised Conditions for Reductive Amidation and Separation of Epimers

Iftikhar

Wang

Fang

2017

Journal of Chemical Research

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1-Deoxynojirimycin (DNJ), which has importance with respect to sugar processing enzymes, is a synthetic target for chemists. A key step in the synthesis of DNJ is the preparation of 2,3,4,6-tetra- O-benzyl-D-glucono-δ-lactam. By varying reaction parameters such as temperature, solvent and reducing reagent, improvements on previous methods are described. A novel approach for the synthesis of 2,3,4,6-tetra- O-benzyl-5-dehydro-5-deoxo-D-gluconamide has been developed by using PCC as an oxidising agent. Separation of epimers permitted DNJ to be obtained in 85% yield after reduction and hydrogenolysis steps.

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Section: Methodsmentioning

confidence: 99%

Section: 346-tetra-o-benzyl-α-d-gluco-methyl-pyranoside (2) 26mentioning

confidence: 99%

Section: 346-tetra-o-benzyl-d-gluconamide (4) 25mentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis of 1-Deoxynojirimycin: Exploration of Optimised Conditions for Reductive Amidation and Separation of Epimers

Iftikhar

Wang

Fang

2017

Journal of Chemical Research

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“…We previously reported the syntheses of extended 1,3‐oxazines as chiral building blocks (Scheme ); we successfully applied them to the syntheses of conduramine F‐1,[10a] (+)‐hyacinthacine A 2 ,[10b] (–)‐sphingofungin B,[10b] (+)‐1‐deoxynojirimycin, 2,5‐dihydroxymethyl‐3,4‐dihydroxypyrrolidine [(+)‐DMDP], (+)‐2,5‐dideoxy‐2,5‐imino‐ d ‐glucitol [(+)‐DGDP],[10c] and (–)‐1‐deoxymannojirimycin [(–)‐DMJ]. [10c] As part of an ongoing research program aimed at the development of syntheses of biologically active compounds, we herein report the stereoselective syntheses of (+)‐broussonetine D ( 1 ) and (+)‐australine ( 2 ) via a functionalized pyrrolidine from an extended chiral 1,3‐oxazine.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Syntheses of (+)‐Broussonetine D and (+)‐Australine via a Functionalized Pyrrolidine from an Extended Chiral 1,3‐Oxazine

Myeong

Ham

2018

Eur J Org Chem

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The asymmetric syntheses of (+)‐broussonetine D and (+)‐australine have been achieved via a functionalized pyrrolidine obtained from an extended chiral 1,3‐oxazine. The key steps include pyrrolidine formation by oxazine cleavage and diastereoselective allylation to a pyrrolidine aldehyde. (+)‐Broussonetine D and (+)‐australine were synthesized from anti,syn,syn‐oxazine, in six steps, with an overall yield of 22.2 %, and in seven steps, with an overall yield of 33.2 %.

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Pyrazole scaffold‐based derivatives: A glimpse of α‐glucosidase inhibitory activity, SAR, and route of synthesis

Firdaus

Siddiqui

Alam

et al. 2023

Archiv der Pharmazie

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The α-glucosidase is a validated target to develop drugs for treating type 2 diabetes mellitus. The existing α-glucosidase inhibitors have certain shortcomings related to side effects and route of synthesis. Accordingly, it is inevitable to develop new chemical templates as α-glucosidase inhibitors. Pyrazole derivatives have a special place in medicinal chemistry because of various biological activities. Recently, pyrazole-based heterocyclic compounds have emerged as a promising scaffold to develop α-glucosidase inhibitors. This study focuses on the recently reported pyrazole-based α-glucosidase inhibitors, including their biological activity (in vivo, in vitro, and in silico), structure-activity relationship, and ways of synthesis. The literature revealed the development of several promising pyrazole-based α-glucosidase inhibitors and new synthetic routes for their preparation. The encouraging α-glucosidase inhibitory results of the pyrazole-based heterocyclic compounds make them an attractive target for further research. The authors also foresee the arrival of the pyrazole-based α-glucosidase inhibitors in clinical practice.

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1,3-Oxazine as a chiral building block used in the total synthesis of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine

Cited by 24 publications

References 45 publications

Synthesis of 1-Deoxynojirimycin: Exploration of Optimised Conditions for Reductive Amidation and Separation of Epimers

Synthesis of 1-Deoxynojirimycin: Exploration of Optimised Conditions for Reductive Amidation and Separation of Epimers

Stereoselective Syntheses of (+)‐Broussonetine D and (+)‐Australine via a Functionalized Pyrrolidine from an Extended Chiral 1,3‐Oxazine

Pyrazole scaffold‐based derivatives: A glimpse of α‐glucosidase inhibitory activity, SAR, and route of synthesis

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