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Volumn 46, Issue 32, 2005, Pages 5297-5300

The first asymmetric synthesis of (2S,3S,4R)-3-amino-2-hydroxymethyl-4- hydroxypyrrolidine

Author keywords

Amino pyrrolidine; Glycosidase inhibitor; Tethered aminohydroxylation

Indexed keywords

3 AMINO 2 HYDROXYMETHYL 4 HYDROXYPYRROLIDINE; ALKENE; AMINOALCOHOL; CARBAMIC ACID DERIVATIVE; HYDROXYPROLINE; OXAZOLIDINONE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 21844445603     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.025     Document Type: Article
Times cited : (22)

References (28)
  • 18
    • 14544306449 scopus 로고    scopus 로고
    • For tethered aminohydroxylation reactions of homoallylic sulfamate esters and sulfonamides see, M.N. Kenworthy, and R.J.K. Taylor Org. Biomol. Chem. 3 2005 603 611
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 603-611
    • Kenworthy, M.N.1    Taylor, R.J.K.2
  • 19
    • 21844434156 scopus 로고    scopus 로고
    • note
    • All new compounds gave satisfactory spectroscopic and microanalytical and/or HRMS analysis.
  • 22
    • 21844459700 scopus 로고    scopus 로고
    • note
    • Attempts to introduce the phenylselenide moiety by reaction of either 9 or 10 under similar conditions were less successful resulting in the isolation of 16 (10%) from 9 and 17 (25%) and 18 (25%) from 10 as the only identifiable products.
  • 23
    • 21844457353 scopus 로고    scopus 로고
    • note
    • 2S requires 297.0909).
  • 24
    • 21844435408 scopus 로고    scopus 로고
    • note
    • 2S requires: C, 49.99; H, 5.16; N, 8.97.
  • 25
    • 21844456579 scopus 로고    scopus 로고
    • note
    • 1 = 0.0813 (for 5413 reflections with I > 2σ(I)) and wR2 = 0.2176 for all data. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers: 6, CCDC 269573; 13, CCDC 269574. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44 (0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ).
  • 27
    • 21844437021 scopus 로고    scopus 로고
    • note
    • The same hydrolysis could also be applied to a mixture of the isomers 6 and 13 to give 14 in 68% yield.
  • 28
    • 21844450540 scopus 로고    scopus 로고
    • note
    • 2), 58.10 (CH), 67.79 (CH).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.