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2-propen-1-yl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-D-glucopyranoside | 1159181-14-2

中文名称
——
中文别名
——
英文名称
2-propen-1-yl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-D-glucopyranoside
英文别名
[(2S,3S,4S,5R,6R)-4,5-dibenzoyloxy-2-(fluoromethyl)-6-prop-2-enoxyoxan-3-yl] benzoate
2-propen-1-yl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-D-glucopyranoside化学式
CAS
1159181-14-2
化学式
C30H27FO8
mdl
——
分子量
534.538
InChiKey
GQGUFDNMDQANTI-YFIKXWTHSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    5.8
  • 重原子数:
    39
  • 可旋转键数:
    13
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.23
  • 拓扑面积:
    97.4
  • 氢给体数:
    0
  • 氢受体数:
    9

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    参考文献:
    名称:
    DAST-Mediated Regioselective Anomeric Group Migration in Saccharides
    摘要:
    When saccharides bearing a sulfur, selenium, or oxygen substituent at the anomeric center and an unprotected hydroxyl group either at C-4 or C-6 were subjected to fluorination with DAST in dichloromethane, a regioselective migration of the anomeric substituent to the C-4 or C-6 position was observed. Certain saccharides gave a mixture of migration and normal fluorination products whereas others yielded mainly or exclusively migration products (beta-glycosyl fluorides). The high thermal and chemical stability of migrated glycosyl fluorides were demonstrated to be an important precursor for many significant carbohydrate analogies. It is therefore suggested that these migrations may have useful applications in organic synthesis.
    DOI:
    10.1021/jo900516r
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文献信息

  • DAST-Mediated Regioselective Anomeric Group Migration in Saccharides
    作者:Po-Chiao Lin、Avijit Kumar Adak、Shau-Hua Ueng、Li-De Huang、Kuo-Ting Huang、Ja-an Annie Ho、Chun-Cheng Lin
    DOI:10.1021/jo900516r
    日期:2009.6.5
    When saccharides bearing a sulfur, selenium, or oxygen substituent at the anomeric center and an unprotected hydroxyl group either at C-4 or C-6 were subjected to fluorination with DAST in dichloromethane, a regioselective migration of the anomeric substituent to the C-4 or C-6 position was observed. Certain saccharides gave a mixture of migration and normal fluorination products whereas others yielded mainly or exclusively migration products (beta-glycosyl fluorides). The high thermal and chemical stability of migrated glycosyl fluorides were demonstrated to be an important precursor for many significant carbohydrate analogies. It is therefore suggested that these migrations may have useful applications in organic synthesis.
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