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Volumn 52, Issue 26, 1996, Pages 8685-8702

Synthesis and asymmetric alkylation of glucose-derived bicyclic oxazinones: An evaluation of their use as "chiral glycines"

Author keywords

[No Author keywords available]

Indexed keywords

1,4 OXAZINE DERIVATIVE; CARBOHYDRATE DERIVATIVE; PYRANO[3,2 B][1,4]OXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030008431     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00431-0     Document Type: Article
Times cited : (15)

References (29)
  • 3
    • 0010438665 scopus 로고
    • The value of the C-2 OH in directing diastereoselective reactions of ligands attached at the anomeric centre has been previously recognized: Charette, A. B.; Mellon, C.; Rouillard, L.; Malenfant, E. Pure Appl. Chem. 1992, 64, 1925-1931.
    • (1992) Pure Appl. Chem. , vol.64 , pp. 1925-1931
    • Charette, A.B.1    Mellon, C.2    Rouillard, L.3    Malenfant, E.4
  • 6
    • 0027626394 scopus 로고
    • A Chemical Abstracts Online search did not reveal examples of bicyclic pyranose derivatives related to 4. A similar 1,4-dioxan-2-one intermediate was proposed in an anomalous acetylation of a (carboxymethyl)-lactoside, although it was not isolated: Dean, B.; Oguchi, H.; Cai, S.; Otsuji, E.; Tashiro, K.; Hakomori, S.; Toyokuni, T. Carbohydr. Res., 1993, 245, 175-192.
    • (1993) Carbohydr. Res. , vol.245 , pp. 175-192
    • Dean, B.1    Oguchi, H.2    Cai, S.3    Otsuji, E.4    Tashiro, K.5    Hakomori, S.6    Toyokuni, T.7
  • 12
    • 0040479649 scopus 로고    scopus 로고
    • t-BOC is clearly a better choice, but conditions to introduce t-BOC into amine 2b have thus far eluded us
    • t-BOC is clearly a better choice, but conditions to introduce t-BOC into amine 2b have thus far eluded us.
  • 15
    • 0039294767 scopus 로고    scopus 로고
    • The reactions of 4d,e were essentially identical at all temperatures tested between -100 °C and -65 °C. For operational simplicity, most experiments were conducted in dry ice/acetone baths at -65 °C
    • The reactions of 4d,e were essentially identical at all temperatures tested between -100 °C and -65 °C. For operational simplicity, most experiments were conducted in dry ice/acetone baths at -65 °C.
  • 22
    • 0001459021 scopus 로고
    • and references therein
    • Williams, R. M. Aldrichimica Acta, 25, 11-25, 1992 and references therein.
    • (1992) Aldrichimica Acta , vol.25 , pp. 11-25
    • Williams, R.M.1
  • 26
    • 85136537563 scopus 로고    scopus 로고
    • 13C resonances are obscured by the solvent signals
    • 13C resonances are obscured by the solvent signals.
  • 27
    • 85136605559 scopus 로고    scopus 로고
    • 13C data were obtained in an HSQC experiment, thus the shifts of non-protonated carbons are absent
    • 13C data were obtained in an HSQC experiment, thus the shifts of non-protonated carbons are absent.


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