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methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-α-D-gluco-pyranoside | 23487-07-2

中文名称
——
中文别名
——
英文名称
methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-α-D-gluco-pyranoside
英文别名
methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-α-D-glucopyranoside;[(2R,3R,4R,5R,6S)-4,5-dibenzoyloxy-3-iodo-6-methoxyoxan-2-yl]methyl benzoate
methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-α-D-gluco-pyranoside化学式
CAS
23487-07-2
化学式
C28H25IO8
mdl
——
分子量
616.406
InChiKey
JVFAWPRLKHELNU-NRUNVSGISA-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):
    4.47
  • 重原子数:
    37.0
  • 可旋转键数:
    8.0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.25
  • 拓扑面积:
    97.36
  • 氢给体数:
    0.0
  • 氢受体数:
    8.0

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
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-α-D-gluco-pyranoside 作用下, 以 乙醇 为溶剂, 反应 6.0h, 以82.3%的产率得到methyl 2,3,6-tri-O-benzoyl-4-deoxy-α-D-xylo-hexopyranoside
    参考文献:
    名称:
    Synthesis of 4-deoxy-d-xylo-hexose and 4-azido-4-deoxy-d-glucose and their effects on lactose synthase
    摘要:
    Syntheses are reported of 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose as potential inhibitors for lactose synthase [uridine 5'-(alpha-D-galactopyranosyl pyrophosphate):D-glucose 4-beta-D-galactopyranosyltransferase, EC 2.4.1.22]. These syntheses involved SN2 displacement of the 4-methylsulfonyloxy group of methyl 2,3,6-tri-O-benzoyl-4-O-methylsulfonyl-alpha-D-galactopyranoside by iodide and azide ions. In both cases, inversion in configuration was observed. The resulting intermediates, methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-alpha-D-glucopyranoside and methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-alpha-D-glucopyranoside, were obtained in crystalline form. Both 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose were found to be inhibitors for lactose synthase in the presence of alpha-lactalbumin, but had no effect in the absence of alpha-lactalbumin. Both D-glucose analogues bind to the enzyme system far more weakly than D-glucose, suggesting that the recognition of the 4-OH group of the acceptor substrate is an important factor in binding.
    DOI:
    10.1016/s0008-6215(00)85655-4
  • 作为产物:
    描述:
    methyl 2,3,6-tri-O-benzoyl-4-O-mesyl-α-D-galactopyranoside 在 sodium iodide 作用下, 以 N,N-二甲基甲酰胺 为溶剂, 以60%的产率得到methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-α-D-gluco-pyranoside
    参考文献:
    名称:
    Synthesis of 4-deoxy-d-xylo-hexose and 4-azido-4-deoxy-d-glucose and their effects on lactose synthase
    摘要:
    Syntheses are reported of 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose as potential inhibitors for lactose synthase [uridine 5'-(alpha-D-galactopyranosyl pyrophosphate):D-glucose 4-beta-D-galactopyranosyltransferase, EC 2.4.1.22]. These syntheses involved SN2 displacement of the 4-methylsulfonyloxy group of methyl 2,3,6-tri-O-benzoyl-4-O-methylsulfonyl-alpha-D-galactopyranoside by iodide and azide ions. In both cases, inversion in configuration was observed. The resulting intermediates, methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-alpha-D-glucopyranoside and methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-alpha-D-glucopyranoside, were obtained in crystalline form. Both 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose were found to be inhibitors for lactose synthase in the presence of alpha-lactalbumin, but had no effect in the absence of alpha-lactalbumin. Both D-glucose analogues bind to the enzyme system far more weakly than D-glucose, suggesting that the recognition of the 4-OH group of the acceptor substrate is an important factor in binding.
    DOI:
    10.1016/s0008-6215(00)85655-4
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文献信息

  • Giese, Bernd; Gilges, Stefan; Groeninger, Kay S., Liebigs Annalen der Chemie, 1988, p. 615 - 617
    作者:Giese, Bernd、Gilges, Stefan、Groeninger, Kay S.、Lamberth, Clemens、Witzel, Tom
    DOI:——
    日期:——
  • GIESE, BERND;GILGES, STEFAN;GRONINGER, KAY S.;LAMBERTH, CLEMENS;WITZEL, T+, LIEBIGS ANN. CHEM.,(1988) N 6, 615-617
    作者:GIESE, BERND、GILGES, STEFAN、GRONINGER, KAY S.、LAMBERTH, CLEMENS、WITZEL, T+
    DOI:——
    日期:——
  • Giese, Bernd; Witzel, Tom, Angewandte Chemie, 1986, vol. 98, # 5, p. 459 - 460
    作者:Giese, Bernd、Witzel, Tom
    DOI:——
    日期:——
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