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Volumn 3, Issue 21, 2001, Pages 3285-3288

A ring-closing metathesis strategy to phosphonosugars

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; HEXOSE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS ACID DERIVATIVE; SINGLE HETEROCYCLIC RINGS;

EID: 0035909597     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016491p     Document Type: Article
Times cited : (43)

References (48)
  • 24
    • 0031966184 scopus 로고    scopus 로고
    • See also ref 3b
    • (c) Brel, V. K. Synthesis 1998, 710-712. See also ref 3b.
    • (1998) Synthesis , pp. 710-712
    • Brel, V.K.1
  • 26
    • 0042773327 scopus 로고    scopus 로고
    • note
    • 31P NMR spectra of the crude reaction mixtures.
  • 27
    • 0042773328 scopus 로고    scopus 로고
    • note
    • Reaction in pure THF gave lower selectivity (3.5:1). Reaction in DME, without HMPA, was sluggish and did not go to completion.
  • 28
    • 0042272211 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry of this compound was determined by single-crystal X-ray crystallography.
  • 35
    • 0042773325 scopus 로고    scopus 로고
    • note
    • Displacement of the phenoxy group in acyclic mixed phenyl phosphonates occurs with inversion of the configuration; see ref 6.
  • 40
    • 0041771425 scopus 로고    scopus 로고
    • Attempts to deprotect the free diol led to decomposition
    • Attempts to deprotect the free diol led to decomposition.
  • 41
    • 85022880129 scopus 로고
    • Deprotection with CAN gave considerably lower yields. For oxidation of 1,4-dimethoxybenzene in the presence of pyridinecarboxylic acids, see: Syper, L.; Klock, K. Mlochowski, J.; Szulc, Z. Synthesis 1979, 36, 123-129. Syper, L.; Mlochowski, J. Tetrahedron 1980, 521-522.
    • (1979) Synthesis , vol.36 , pp. 123-129
    • Syper, L.1    Klock, K.2    Mlochowski, J.3    Szulc, Z.4
  • 42
    • 0042272210 scopus 로고
    • Deprotection with CAN gave considerably lower yields. For oxidation of 1,4-dimethoxybenzene in the presence of pyridinecarboxylic acids, see: Syper, L.; Klock, K. Mlochowski, J.; Szulc, Z. Synthesis 1979, 36, 123-129. Syper, L.; Mlochowski, J. Tetrahedron 1980, 521-522.
    • (1980) Tetrahedron , pp. 521-522
    • Syper, L.1    Mlochowski, J.2
  • 47
    • 0043274630 scopus 로고    scopus 로고
    • note
    • It is worth noting that attempts for dihydroxylation without citric acid gave only unreacted starting material.
  • 48
    • 0042272209 scopus 로고    scopus 로고
    • note
    • Donohoe attributed the difference in selectivity to the orientation of the hydroxyl group; the trans-isomer bearing a locked axial hydroxy group gave higher selectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.