57492-90-7Relevant academic research and scientific papers
A stereoselective and efficient route to (3S, 4R, 5S)-(+)-4,5- dihydroxycyclopent-1-en-3-ylamine: The side chain of the hypermodified nucleoside Q
Ovaa, Huib,Codee, Jeroen D. C.,Lastdrager, Bas,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Van Boom, Jacques H.
, p. 7987 - 7990 (1998)
A stereoselective and high yielding route is described to a suitably protected derivative of (3S, 4R, 5S)-(+)-3-amino-4,5-dihydroxycyclopent-1- ene, the side chain moiety of queuosine. The synthetic route comprises a ring-closing metathesis (RCM) of a mannofuranose-derived diene followed by Overman rearrangement.
Chiron Approach for the Total Synthesis of Brevipolide M
Liu, Yang,Zhao, Ziyang,Hu, Chao,Zhao, Chuanfang,Liu, Jun,Du, Yuguo
, p. 478 - 482 (2022/02/23)
An efficient stereoselective synthesis of brevipolide M was established in 13 linear steps and 17.8% overall yields based on chiron approach. The key steps of our synthesis involved tandem Wittig olefination tetrahydrofuran cyclization and sequential ring
Selective deprotection of terminal isopropylidene acetals and trityl ethers using HClO4 supported on silica gel
Agarwal, Aditi,Vankar, Yashwant D.
, p. 1661 - 1667 (2007/10/03)
Terminal isopropylidene acetals are selectively cleaved to the corresponding 1,2-diols in good to excellent yields in 6-24 h at room temperature by using the 'HClO4?SiO2' reagent system. Likewise, trityl ethers are readily cleaved to the corresponding alcohols in good to excellent yields within 2-3 h at room temperature. Work-up involves merely filtration of the reagent followed by purification of the crude product.
Synthesis of novel 1α,25-dihydroxy-19-norvitamin D3 with an amide conjugate
Suhara, Yoshitomo,Ono, Keiichiro,Yoshida, Akihiro,Fujishima, Toshie,Saito, Nozomi,Honzawa, Shinobu,Kishimoto, Seishi,Sugiura, Takayuki,Waku, Keizo,Takayama, Hiroaki,Kittaka, Atsushi
, p. 423 - 436 (2007/10/03)
The diene system of 1α,25-dihydroxy-19-norvitamin D3 was replaced by a stable amide bond. A 3-hydroxypropoxy group, which was effective on enhancing binding affinity of 1α,25-dihydroxyvitamin D3 for vitamin D receptor (VDR), was introduced to the C2-position of the amide type analogue of 1α,25-dihydroxy-19-norvitamin D3. The amide analogue was found to be not suitable for binding to the ligand binding domain of the bovine thymus VDR, and additional modification at the C2-position did not improve the affinity. Potency in induction of HL-60 cell differentiation was evaluated for the novel amide analogues (3a-c).
Infrared and Nuclear Magnetic Resonance Properties of Benzoyl Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
Jeon, Kyu Ok,Jun, Jung Ho,Yu, Ji Sook,Lee, Chang Kiu
, p. 763 - 771 (2007/10/03)
Benzophenones, 2-benzoylthiophenes, 2-benzoylpyrroles, and 2-benzoylfurans, which have substituents at m- and p-positions of the benzoyl ring were prepared and their ir and nmr spectra were obtained in 0.1 M chloroform-d solution. The chemical shift values of each series were plotted against the Hammett substituent parameters to give good correlation, with the exception of the ortho-Hs and -Cs. The slopes as well as the differences in chemical shift gave sets of meaningful values for the indices of aromaticy.
Aflexible synthesis of cyclopentitol derivatives based on ring-closing metathesis of carbohydrate-derived 1,6-dienes
Ovaa, Huib,Lastdrager, Bas,Codee, Jeroen D. C.,Van der Marel, Gijs A.,Overkleeft, Herman S.,Van Boom, Jacques H.
, p. 2370 - 2377 (2007/10/03)
Four partially protected stereoisomeric cyclopentenetriols 5, 10, 15 and 21 have been prepared by ring-closing metathesis of carbohydrate-derived 1,6-dienes. The presence of a differentiated allylic alcohol in the cyclopentenetriols allows a variety of synthetic transformations, underlining the synthetic use of the prepared cyclopentenetriol derivatives as chiral building blocks.
The role of the C-3 substituent in the asymmetric dihydroxylation of hexo-5-enofuranosides
Mereyala, Hari Babu,Goud, P. Mallikarjun,Gadikota, Rajendrakumar Reddy,Maddala, Rama Krishna,Reddy, K. Ramasubba
, p. 1201 - 1210 (2007/10/03)
Asymmetric dihydroxylation of vinyl furanosides 1-6 by use of OsO4, AD-mix-α and β is described yielding the corresponding hexofuranose sugars. Vinyl furanosides 2 and 3, with an ester group at C-3, and vinyl manno furanoside 5 on asymmetric dihydroxylation with AD-mix α exhibited high R diastereoselectivity at C-5. Reversal in diastereoselectivity at C-5 was observed for the 3-deoxy vinyl furanoside 6 giving furanosaccharide 6S with the S configuration at C-5.
An efficient, selective hydrolysis of terminal isopropylidene acetal protection by Zn(NO3)2·6H2O in acetonitrile
Vijayasaradhi,Singh, Jaimala,Aidhen, Indrapal Singh
, p. 110 - 112 (2007/10/03)
Di-O-isopropylidene sugar derivatives (1a-9a) on treatment with a solution of Zn(NO3)2·6H2O in acetonitrile, undergo regioselective hydrolysis to furnish the corresponding diols (1b-9b) in excellent yields.
A Simple Regioselective Partial Hydrolysis of Di-O-isopropylidene Monosaccharides with Copper(II) Ion
Iwata, Masaaki,Ohrui, Hiroshi
, p. 2837 - 2838 (2007/10/02)
Copper(II) ion was found to be effective for regioselective removal of the 5,6-O-isopropylidene group of α-D-mannose and α-D-glucose derivatives in alcohols at ambient temperature.
