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

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 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
• CAS: 23487-07-2
• 化学式: C₂₈H₂₅IO₈
• 分子量: 616.406
• InChiKey: JVFAWPRLKHELNU-NRUNVSGISA-N

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

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 在 镍 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

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：——