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Volumn 3, Issue 24, 2001, Pages 3899-3902

Enantioselective synthesis of N-Cbz-protected 6-amino-6-deoxymannose, -talose, and -gulose

Author keywords

[No Author keywords available]

Indexed keywords

6 AMINO 6 DEOXYGLUCOPYRANOSE; 6 AMINO 6 DEOXYMANNOSE; 6 AMINO 6 DEOXYTALOSE; 6-AMINO-6-DEOXYGLUCOPYRANOSE; 6-AMINO-6-DEOXYMANNOSE; 6-AMINO-6-DEOXYTALOSE; AMINOSUGAR; DRUG DERIVATIVE; GLUCOSAMINE; RHAMNOSE;

EID: 0035969619     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016743m     Document Type: Article
Times cited : (51)

References (51)
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    • The absolute stereochemistry and the level of enantioexcesses of 3 and 6 were determined by the method of Mosher, see ref 20a
    • The absolute stereochemistry and the level of enantioexcesses of 3 and 6 were determined by the method of Mosher, see ref 20a.
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    • note
    • Our optimized variation from the typical Sharpless procedure was to the use the sodium salt of N-chlorobenzylcarbamate as the limiting reagent, providing a good yield of a mixture of regioisomers (74%). Thus, the volatile and inexpensively produced vinylfuran in 30% excess allowed for more efficient use of the more costly catalyst and chiral ligand. This procedure routinely provided a ∼40% yield of the furfuryl alcohol 3 and a 21% yield of the TBS-protected regioisomer, see ref 19.
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    • In our hands, the TON (turn over numbers) for the catalytic (10%) use of the oxazaborolidine was too low for practical use
    • In our hands, the TON (turn over numbers) for the catalytic (10%) use of the oxazaborolidine was too low for practical use.
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    • The preceding reaction sequences have been preformed on both (+)-3 and (-)-3; for simplicity reasons we are only drawing the results for (+)-3
    • The preceding reaction sequences have been preformed on both (+)-3 and (-)-3; for simplicity reasons we are only drawing the results for (+)-3.
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    • note
    • By performing the reaction at higher temperatures (0 °C), the minor isomer pivaloate 14β could also be obtained in higher yields as part of a 3:2 ratio, still favoring of the α-anomer 14α. At this point the anomers were separated by medium-pressure liquid chromatography (MPLC, 20% EtOAc/hexanes, UV detection) which produced baseline separation.
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    • note
    • A simpler purification procedure resulted by carrying the ∼8% impurity of the minor diastereoisomer through to the reduction step. The β-anomer 14β presumably hydrolyzed when subjected to the Luche conditions; thus when samples of 14α were reduced with small amounts of the β-anomer present, only diastereomerically pure samples of 2 were detected after silica gel chromatography.
  • 50
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    • The relative stereochemistry of the p-nitrobenzoate ester was confirmed by single-crystal X-ray analysis, see Supporting Information
    • The relative stereochemistry of the p-nitrobenzoate ester was confirmed by single-crystal X-ray analysis, see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.