메뉴 건너뛰기




Volumn 10, Issue 4, 1999, Pages 689-703

Stereochemistry of addition of carbanion reagents to 'diacetone fructose aldehyde'. Configurational assignment of a 1-deoxyheptulose derivative by X- ray crystallography and NMR studies directed to the assignment of isomeric adducts

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYHEPTULOSE DERIVATIVE; ACETONYLACETONE; ALDEHYDE; FRUCTOSE; SULFAMIC ACID DERIVATIVE; TOPIRAMATE; UNCLASSIFIED DRUG;

EID: 0033605048     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00035-X     Document Type: Article
Times cited : (2)

References (45)
  • 4
    • 0027247358 scopus 로고
    • (d) Follow-up reviews: Anon. Ibid. 1993, 18, 397-398; Anon. Ibid. 1994, 19, 425; Anon. Ibid. 1995, 20, 444-445; Anon. Ibid. 1997, 22, 458-460;
    • (1993) Drugs Future , vol.18 , pp. 397-398
  • 5
    • 0028228164 scopus 로고
    • (d) Follow-up reviews: Anon. Ibid. 1993, 18, 397-398; Anon. Ibid. 1994, 19, 425; Anon. Ibid. 1995, 20, 444-445; Anon. Ibid. 1997, 22, 458-460;
    • (1994) Drugs Future , vol.19 , pp. 425
  • 6
    • 0029055376 scopus 로고
    • (d) Follow-up reviews: Anon. Ibid. 1993, 18, 397-398; Anon. Ibid. 1994, 19, 425; Anon. Ibid. 1995, 20, 444-445; Anon. Ibid. 1997, 22, 458-460;
    • (1995) Drugs Future , vol.20 , pp. 444-445
  • 7
    • 0344678877 scopus 로고    scopus 로고
    • (d) Follow-up reviews: Anon. Ibid. 1993, 18, 397-398; Anon. Ibid. 1994, 19, 425; Anon. Ibid. 1995, 20, 444-445; Anon. Ibid. 1997, 22, 458-460;
    • (1997) Drugs Future , vol.22 , pp. 458-460
  • 20
    • 0344678873 scopus 로고    scopus 로고
    • note
    • (b) The samples of 2 and 3 examined for anti-convulsant activity were enriched in the R-isomer (2a/3a) and were virtually devoid of activity (see Ref. 3a) We did not have the opportunity to prepare and test samples enriched in the 5-isomer (2b/3b).
  • 22
    • 0345109769 scopus 로고    scopus 로고
    • personal communication
    • In fact, a recent discussion (Heathcock, C. H., personal communication, 1997) confirmed that the configuration in question is not established by Ref. 4.
    • (1997)
    • Heathcock, C.H.1
  • 25
    • 0345109767 scopus 로고    scopus 로고
    • Izquierdo et al. (see Ref. 7) also reported that 6 reacts with dimethylsulfonium methoxycarbonylmethylide (in THF:DMSO, 23°C → 60°C) to afford a single product, the (b)-epoxide;
    • (a) Izquierdo et al. (see Ref. 7) also reported that 6 reacts with dimethylsulfonium methoxycarbonylmethylide (in THF:DMSO, 23°C → 60°C) to afford a single product, the (b)-epoxide;
  • 26
    • 0004710596 scopus 로고
    • (b) The addition of cyanide to 6 was reported (Kuszmann, J.; Marton-Meresz, M.; Jerkovich, G. Carbohydr. Res. 1988, 175, 249-264) to give an 85:15 ratio of cyanohydrins (ether:water, 23°C), but an assignment of stereochemistry was not made. Although this addition showed a strong stereochemical bias, it probably resulted from equilibrium control, rather than kinetic control.
    • (1988) Carbohydr. Res. , vol.175 , pp. 249-264
    • Kuszmann, J.1    Marton-Meresz, M.2    Jerkovich, G.3
  • 29
    • 0344678870 scopus 로고    scopus 로고
    • note
    • The fairly constant yields for adducts 11 are a consequence of a balance between the amounts of reduction product 10 and unreacted aldehyde 6.
  • 42
    • 0345109762 scopus 로고    scopus 로고
    • note
    • It should be noted that the presentation of chair structures for such tricyclic sugars in references 6 and 7 is not consistent with the expected skew conformation (see Refs 14 and 15).
  • 45
    • 0345109759 scopus 로고    scopus 로고
    • note
    • Tables of bond distances, bond angles, and positional and thermal parameters are available on request from the corresponding author.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.