INTRAMOLECULAR C-GLYCOSIDATION OF SUBSTITUTED SUGARS
取代糖的分子内 C-糖苷化
基本信息
- 批准号:3295325
- 负责人:
- 金额:$ 8.72万
- 依托单位:
- 依托单位国家:美国
- 项目类别:
- 财政年份:1987
- 资助国家:美国
- 起止时间:1987-07-01 至 1990-06-30
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
A novel methodology for the stereospecific synthesis of C-
glycosides is proposed. This methodology is based on the
preliminary attachment of a substituent containing a latent
carbon-nucleophilic function to one of the hydroxyl function of a
cyclic sugar derivative, followed by the creation of a carbon-
carbon bond between this group and the anomeric center of the
sugar. Thus, O-benzylated, N-benzylated and O-phenylated sugars
should lead to "internal" C-glycosides (isochromans,
tetrahydroisoquinolines and 2,3-dihydrobenzofurans resp.) which
could be cleaved to C-glycosylated benzene derivatives or further
elaborated (for example into tetrahydroisoquinoline alkaloids).
The one-step transfer of a C-nucleophile might be achieved using
a difunctional silyl derivative as a temporary linkage to the sugar-
hydroxyl function: thus O-aryloxysilyl, as well as O-aryl-and O-
allyl-dimethylsilyl carbohydrate derivatives are expected to
undergo intra-molecular C-glycosidation with simultaneous
cleavage of the auxiliary linkage upon treatment with a Lewis
acid, thereby providing a highly efficient and general method of
stereospecific C-glycosidation.
This methodology will be used for the synthesis of a number of
biologically and pharmacologically significant structures. Thus a
series of arabino nucleoside analogs, in particular the dideaza
analog of ara-C, one of the most potent agents against acute
leukemia, benzenoid analogs of cyclouridine and cyclocytidine, as
well indole C-nucleosides related to the antiviral agent are-A will
be prepared by the intramolecular C-glycosylation of suitably
substituted benzene and indole derivatives. The proposed
methodology provides also a short approach to natural internal C-
glycosides such as bergenin and related compounds, as well as to
C-glycosyl flavonoids. Furthermore, N-benzylated amino sugars
are precursors of chiral tetrahydroisoquinolines which have an
extremely interesting substitution pattern because of its relation
to that of tetra-hydroisoquinolines derived from biogenic amines
and certain psychopharmacological drugs. C-benzylation of the
corresponding N-benzylidene imino sugars, expected to be highly
stereoselective, gives an intermediate which should lead in one
step, by a "double intramolecular C-arylation" process, to the
skeleton of the isopavine alkaloids. These reactions provide a
short synthetic route from carbohydrates to chiral tetra-
hydroisoquinoline alkaloids.
一种立体定向合成 C- 的新方法
建议配糖体。 该方法基于
初步连接含有潜在的取代基
碳亲核官能团与羟基官能团之一
环糖衍生物,然后创建碳-
该基团与异头中心之间的碳键
糖。 因此,O-苯甲基化、N-苯甲基化和O-苯基化糖
应该导致“内部”C-糖苷(异色满,
四氢异喹啉和 2,3-二氢苯并呋喃)
可以裂解成C-糖基化苯衍生物或进一步
精制(例如四氢异喹啉生物碱)。
C-亲核试剂的一步转移可通过以下方法实现
双官能硅基衍生物作为糖的临时连接
羟基官能团:因此O-芳氧基甲硅烷基,以及O-芳基-和O-
烯丙基二甲基甲硅烷基碳水化合物衍生物预计
同时进行分子内 C-糖苷化
用路易斯处理后辅助键的断裂
酸,从而提供了一种高效且通用的方法
立体特异性C-糖苷化。
该方法将用于合成许多
具有生物学和药理学意义的结构。 因此一个
系列阿拉伯核苷类似物,特别是 dideaza
ara-C 类似物,最有效的抗急性药物之一
白血病,环尿苷和环胞苷的苯类似物,如
与抗病毒剂相关的吲哚C-核苷是-A
通过适当的分子内C-糖基化来制备
取代苯和吲哚衍生物。 拟议的
方法论还提供了一种了解自然内部 C 的简短方法
糖苷,例如岩白菜素和相关化合物,以及
C-糖基黄酮类化合物。 此外,N-苄基化氨基糖
是手性四氢异喹啉的前体,具有
由于其关系,替换模式非常有趣
与衍生自生物胺的四氢异喹啉相比
和某些精神药理学药物。 C-苄基化
相应的N-亚苄基亚氨基糖,预计将是高度
立体选择性,给出一种应该导致一个的中间体
步骤,通过“双分子内C-芳基化”过程,
异罂粟碱生物碱的骨架。 这些反应提供了
从碳水化合物到手性四元的短合成路线
氢异喹啉生物碱。
项目成果
期刊论文数量(2)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Multiple and long-range participation of benzyl groups in intramolecular C-arylation reactions of benzylated glycosides.
苄基多次、长程参与苄基化糖苷的分子内C-芳基化反应。
- DOI:10.1016/0008-6215(90)84070-b
- 发表时间:1990
- 期刊:
- 影响因子:3.1
- 作者:Martin,OR;Rao,SP;Hendricks,CA;Mahnken,RE
- 通讯作者:Mahnken,RE
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OLIVIER R MARTIN其他文献
OLIVIER R MARTIN的其他文献
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{{ truncateString('OLIVIER R MARTIN', 18)}}的其他基金
INTRAMOLECULAR C-GLYCOSIDATION OF SUBSTITUTED SUGARS
取代糖的分子内 C-糖苷化
- 批准号:
3295322 - 财政年份:1987
- 资助金额:
$ 8.72万 - 项目类别:
INTRAMOLECULAR C-GLYCOSIDATION OF SUBSTITUTED SUGARS
取代糖的分子内 C-糖苷化
- 批准号:
3295324 - 财政年份:1987
- 资助金额:
$ 8.72万 - 项目类别:
SYNTHESIS AND BIOLOGICAL EVALUATION OF C-DISACCHARIDES
C-二糖的合成和生物学评价
- 批准号:
2139638 - 财政年份:1985
- 资助金额:
$ 8.72万 - 项目类别:
SYNTHESIS AND BIOLOGICAL EVALUATION OF C-DISACCHARIDES
C-二糖的合成和生物学评价
- 批准号:
3154187 - 财政年份:1985
- 资助金额:
$ 8.72万 - 项目类别:
SYNTHESIS AND BIOLOGICAL EVALUATION OF C-DISACCHARIDES
C-二糖的合成和生物学评价
- 批准号:
3234018 - 财政年份:1985
- 资助金额:
$ 8.72万 - 项目类别:
SYNTHESIS AND BIOLOGICAL EVALUATION OF C-DISACCHARIDES
C-二糖的合成和生物学评价
- 批准号:
2139637 - 财政年份:1985
- 资助金额:
$ 8.72万 - 项目类别:
SYNTHESIS AND BIOLOGICAL EVALUATION OF C-DISACCHARIDES
C-二糖的合成和生物学评价
- 批准号:
3234012 - 财政年份:1985
- 资助金额:
$ 8.72万 - 项目类别:
SYNTHESIS AND BIOLOGICAL EVALUATION OF C-DISACCHARIDES
C-二糖的合成和生物学评价
- 批准号:
3234017 - 财政年份:1985
- 资助金额:
$ 8.72万 - 项目类别:
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