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Catalytic Stereoseletive Synthesis of Glycosides

Catalytic Stereoseletive Synthesis of Glycosides
糖苷的催化立体选择性合成
批准号:
08454231
负责人:
MUKAIYAMA Teruaki
金额:
$5.12万
依托单位:
依托单位国家:
日本
项目类别:
Grant-in-Aid for Scientific Research (B)
财政年份:
1996
资助国家:
日本
项目状态:
已结题
起止时间:
1996 至 1997

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中文摘要
翻译
在催化量的四(五氟苯基)硼酸酯(TrB(C_6F_5)_4)存在下,2,3,5-三-O-苯基-D-呋喃核糖与醇反应,高产率、高立体选择性地合成了多种β-D-呋喃核苷。在锂盐共存下,还观察到了反向立体选择性,从2,3,3-三-O-苯基-D-核呋喃糖合成了α-D-呋喃核苷。在LiClO_4或LiNTF_2存在下,5-三-O-苄基-D-呋喃核糖和几种醇发生了反向立体选择,这可能是由于α-异构体通过形成含锂离子的配位络合物而选择性稳定的结果。在呋喃糖苷的合成中,仅从1-羟基糖开始的糖基化反应的立体选择性是令人满意的,但在吡喃糖苷的合成中并不总是如此。在SnOTf_2-Me_3SiCl催化体系和有效添加剂LiC_1O_4的联合作用下,成功地实现了几种醇类亲核试剂与2,3,4,6-四-O-苯基-D-半乳糖(1-羟基糖)的糖基化反应。几个α-D-半乳糖苷以较高的立体选择性得到了几个α-D-半乳糖苷。脱氧糖苷通常存在于蒽环类、金黄色酸、正霉素类和其他有药用价值的化合物的糖组分中。2-脱氧-α-D-糖苷是含糖天然产物中重要的生物结构单元。以3,4,6-三-O-苯基-2-脱氧-D-吡喃葡萄糖(1-羟基糖)为原料,在TrB(C_6F_5)_4催化下,高产率地立体选择性地合成了几种2-脱氧-α-D-吡喃葡萄糖苷。
英文摘要
In the presence of a catalytic amount of trityl tetrakis(pentafluoropheny1) borate (TrB(C_6F_5)_4), 2,3,5-tri-O-benzyl-D-ribofuranose smoothly reacted with alcohols to give various beta-D-ribofuranosides in high yields with high stereoselectivitiy.Reverse stereoselection was also observed in the coexistence of lithium salts, and alpha-D-ribofuranosides were synthesized from 2,3,5-tri-O-benzy1-D-ribofuranose and several alcohols in the presence of LiClO_4 or LiNTf_2. These reverse stereoselection by using lithium salts occurred probably due to the selective stabilization of the alpha-anomer by forming a coordinated complex including lithium cation.The stereoselectivity of the glycosylation starting just from 1-hydroxy sugar in furanoside synthesis was in satisfactory level but not always so in pyranoside synthesis. The glycosylation reaction of several alcoholic nucleophiles with 2,3,4,6-tetra-O-benzy1-D-galactopyranose (1-hydroxy sugar) is successfully carried out by the combined use of Sn(OTf)_2-Me_3SiCl catalyst system andLiC1O_4, an effective additive. Several alpha-D-galactopyranosides are obtained in good yields with high stereoselectivities.Deoxyglycosides are often found in sugar components of anthracyclines, aureoic acids, orthosomycines and in other compounds of pharmaceutical interest. 2-Deoxy-alpha-D-glycosides are known as biologically important structural units in the fields of sugar-containing natural products. Several 2-deoxy-alpha-D-glucopyranosides are stereoselectively synthesized in high yields by glycosylation of various alcoholic nucleophiles with 3,4,6-tri-O-benzy1-2-deoxy-D-glucopyranose (1-hydroxy sugar)using a catalytic amount of TrB (C_6F_5)_4.
期刊论文(38)
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会议论文
Hiromi Uchiro: "An Efficient Method for Catalytic and Stereoselective Glycosylation with Thioglycosides Promoted by Trityl Tetrakis (pentafluorophenyl) borate and Sodium Periodate" Chemistry Letters. 121-122 (1997)
Hiromi Uchiro:“一种由三苯甲基四(五氟苯基)硼酸盐和高碘酸钠促进的硫代糖苷催化和立体选择性糖基化的有效方法”化学快报。
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T.Mukaiyama: "Catalytic Stereoselective Synthesis of Pyrimidine 2-Deoxyribonucleosides" Chem.Lett.99-100 (1996)
T.Mukaiyama:“嘧啶 2-脱氧核糖核苷的催化立体选择性合成”Chem.Lett.99-100 (1996)
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Hiromi Uchiro: "Trityl Salt Catalyzed Stereoselective Glycosylation of Alcohols with 1-Hydroxylribofuranose" Chemistry Letters. 79-80 (1996)
Hiromi Uchiro:“三苯甲基盐催化醇与 1-羟基呋喃核糖的立体选择性糖基化”化学快报。
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Teruaki Mukaiyama: "Highly Stereoselective Synthesis of 2'-Deoxy-α-ribonucleosides and 2-Deoxy-α-ribofuranosides by Remoto Stereocontrolled Glycosylation" Chemistry Letters. 389-390 (1997)
Teruaki Mukaiyama:“通过远程立体控制糖基化高度立体选择性合成 2-脱氧-α-核糖核苷和 2-脱氧-α-呋喃核苷”化学快报 389-390 (1997)。
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共 31 条
    Stereospecific functional group conversion based on oxidation-reduction condensation
    Study for stereoselective synthesis of oligosaccharides by new glycosylation methods
    A New and Stereoselective Glycosylation and Synthesis of Origosuccaride
    • 批准号:
      10440217
    • 项目类别:
      Grant-in-Aid for Scientific Research (B).
    • 资助金额:
      $7.36万
    • 财政年份:
      1998
    • 负责人:
      MUKAIYAMA Teruaki
    • 依托单位:
    Catalytic Stereoselective Synthesis of Glycosides
    • 批准号:
      06453065
    • 项目类别:
      Grant-in-Aid for General Scientific Research (B)
    • 资助金额:
      $5.31万
    • 财政年份:
      1994
    • 负责人:
      MUKAIYAMA Teruaki
    • 依托单位:
    海外基金