2-(3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-gluco-pyranosyl)-thio-2-thiono-5,5-dimethyl-1,3,2-dioxaphosphorinane | 224184-72-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-gluco-pyranosyl)-thio-2-thiono-5,5-dimethyl-1,3,2-dioxaphosphorinane
• CAS: 224184-72-9
• 化学式: C₁₇H₂₆BrO₉PS₂
• 分子量: 549.398
• InChiKey: XJKLMRIFVUCAMR-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  吲哚美辛 、 2-(3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-gluco-pyranosyl)-thio-2-thiono-5,5-dimethyl-1,3,2-dioxaphosphorinane 在 4 A molecular sieve 、 silver carbonate 作用下， 以 苯 为溶剂， 反应 13.0h， 以74%的产率得到1-O-[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetyl]-3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Glycosyl derivatives of 2-bromosugar of selected non-steroidal anti-inflammatory drugs. Synthesis and QSAR data

  摘要：

  On the basis of molecular modeling and calculation of physicochemical SAR data we obtained new derivatives of 2-bromosugars 5a-d and 6 for widely used non-steroidal anti-inflammatory drugs (NSAIDs). Compounds 5a-d and 6 were synthesized as stable, crystalline compounds from the reaction of phosphoroates 1-3 with salicylic acid (4a), aspirin (4b), diclofenac (4c) and indomethacin (4d) in an aprotic solvent. The reaction took place in the presence of silver carbonate as the activator of leaving groups with high stereo selectivity and good yields. The structures of the new derivatives of 5a-d and 6 for NSAIDs were established by spectroscopic methods H-1 and C-13 NMR, and elemental analyses. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01034-5
• 作为产物：
  描述：

  2-thiolo-2-thiono-5,5-dimethyl-1,2,3-dioxaphosphorinane triethylammonium salt 、 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-glucopyranosyl bromide 以 二氯甲烷 为溶剂， 反应 10.0h， 以7%的产率得到2-(3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-gluco-pyranosyl)-thio-2-thiono-5,5-dimethyl-1,3,2-dioxaphosphorinane
  参考文献：
  名称：

  Borowiecka, Polish Journal of Chemistry, 1999, vol. 73, # 5, p. 793 - 798

  摘要：

  DOI：