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INTRAMOLECULAR ADDITION REACTIONS OF 4-O-CARBAMOYL-2,3-UNSATURATED MONOSACCHARIDES

등록일
2005년 8월 11일 13시 55분 13초
접수번호
0871
발표코드
25P188포 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
토 <발표Ⅳ>
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
정현준, 정봉영
고려대학교 화학과,
Ferrier transformation of 3,4,6-tri-O-acetyl-D-glucal with methanol produced D-pseudoglucal. Deacetylation and t-butyldipnenylsilylation of 6-hydroxy group afforded methyl 6-O-(t-butyldiphenylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside. Mitsunob reaction of this 4-hydroxy compound and debenzoylation also afforded methyl 6-O-(t-butyldiphenylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside. Carbamoylation of these two epimeric products yielded methyl 4-O-carbamoyl-6-O-(t-butyldiphenylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside and methyl 4-O-carbamoyl-6-O-(t-butyldiphenylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside, respectively. Intramolecular addition reaction of these compounds in the presence of 10 mol% platinum (IV) chloride and excess amounts of chlorotrimethylsilane at room temperature produced 5-membered cyclic carbamates of 3-amino-2,3-dideoxy sugars. The stereochemistry of these cyclic carbamates was confirmed by NMR spectroscopy.

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