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Volumn 11, Issue 7, 2009, Pages 1527-1530

Protecting group and solvent control of stereo-and chemoselectivity in glucal 3-carbamate amidoglycosylation

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; DRUG DERIVATIVE; GLUCONATE CALCIUM; HEXOSAMINE; MANNOSAMINE; MANNOSE; OXAZOLIDINONE DERIVATIVE;

EID: 64349108311     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900126q     Document Type: Article
Times cited : (36)

References (66)
  • 15
    • 64349110403 scopus 로고    scopus 로고
    • For a strategy of internally directed glycal aminohydroxylation, see
    • For a strategy of internally directed glycal aminohydroxylation, see:
  • 25
    • 64349104870 scopus 로고    scopus 로고
    • Related aziridinations
    • Related aziridinations:
  • 30
  • 36
    • 53849121623 scopus 로고    scopus 로고
    • Another Rh-nitrenoid approach to 2-amino glycosides, using glucal sulfamates: Lorpitthaya, R.; Xie, Z.-Z.; Kuo, J.-L.; Liu, X.-W. Chem. Eur. J. 2008, 14, 1561-1570.
    • Another Rh-nitrenoid approach to 2-amino glycosides, using glucal sulfamates: Lorpitthaya, R.; Xie, Z.-Z.; Kuo, J.-L.; Liu, X.-W. Chem. Eur. J. 2008, 14, 1561-1570.
  • 39
    • 64349111779 scopus 로고    scopus 로고
    • See Supporting Information for carbamate syntheses
    • See Supporting Information for carbamate syntheses.
  • 41
    • 64349102612 scopus 로고    scopus 로고
    • See also footnote 17 of
    • See also footnote 17 of.
  • 45
    • 84869264752 scopus 로고    scopus 로고
    • 2 did not produce byproduct 8b (or any 7b) from 6b. We also noted earlier (ref 8) that tri-O-acetyl-D-glucal does not react under our conditions, though it is a substrate for Kirschning-type oxidation:
    • 2 did not produce byproduct 8b (or any 7b) from 6b. We also noted earlier (ref 8) that tri-O-acetyl-D-glucal does not react under our conditions, though it is a substrate for Kirschning-type oxidation:
  • 56
    • 33750483259 scopus 로고    scopus 로고
    • An alternative would be catalyst-controlled chemoselectivity. In our systems, of various Rh(II) carboxylates examined, only Rh2(OAc) 4 and Du Bois's Rh2(esp)2 provided complete conversion, and neither catalyst was satisfactory in limiting C3-H oxidation. Catalyst control of chemoselectivity in rhodium nitrenoid and carbenoid insertions, respectively: (a) Hayes, C. J, Beavis, P. W, Humphries, L. A. Chem. Commun. 2006, 4501-4502
    • 2 provided complete conversion, and neither catalyst was satisfactory in limiting C3-H oxidation. Catalyst control of chemoselectivity in rhodium nitrenoid and carbenoid insertions, respectively: (a) Hayes, C. J.; Beavis, P. W.; Humphries, L. A. Chem. Commun. 2006, 4501-4502.
  • 61
    • 27844506623 scopus 로고    scopus 로고
    • Since dihydropyranones 8 are Michael acceptors for alcohols under basic or acidic conditions (for example: Mann, B.; Pitts, D.; Koviach, J. J. Carbohydr Chem 2005, 24, 161-168.), we verified their stability under the reaction conditions. See Supporting Information for details.
    • Since dihydropyranones 8 are Michael acceptors for alcohols under basic or acidic conditions (for example: Mann, B.; Pitts, D.; Koviach, J. J. Carbohydr Chem 2005, 24, 161-168.), we verified their stability under the reaction conditions. See Supporting Information for details.
  • 62
    • 85164065766 scopus 로고    scopus 로고
    • H4, H5 determinations.
    • H4, H5 determinations.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.