3-[4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-phenoxy]-propan-1-ol | 848940-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-phenoxy]-propan-1-ol
• CAS: 848940-05-6
• 化学式: C₄₃H₄₆O₈
• 分子量: 690.833
• InChiKey: HPPOICGLYNKVIT-BQLIBBPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  51.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.84
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-[4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-phenoxy]-propan-1-ol 在 吡啶 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 (2S,3R,4S,5R,6R)-2-[4-(3-iodopropoxy)phenoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
  参考文献：
  名称：

  Synthesis of mono-glucose-branched cyclodextrins with a high inclusion ability for doxorubicin and their efficient glycosylation using Mucor hiemalis endo-β-N-acetylglucosaminidase

  摘要：

  The mono-glucose-branched cyclodextrins having an appropriate spacer between the beta-cyclodextrin and a glucose moiety were synthesized from beta-cyclodextrin and arbutin. They had the significantly high association constants for doxorubicin, the anticancer agent, in the range of 10(5)-10(6) M-1, and worked as highly reactive glycosyl acceptors for the transglycosylation reaction by endo-beta-N-acetylglucosaminidase of Mucor hiemalis to produce sialo-complex type oligosaccharide-branched cyclodextrins in the high yields of 65-67%. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.040
• 作为产物：
  描述：

  (2S,3R,4S,5S,6R)-2-(4-Allyloxy-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 3-[4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-phenoxy]-propan-1-ol
  参考文献：
  名称：

  Synthesis of mono-glucose-branched cyclodextrins with a high inclusion ability for doxorubicin and their efficient glycosylation using Mucor hiemalis endo-β-N-acetylglucosaminidase

  摘要：

  The mono-glucose-branched cyclodextrins having an appropriate spacer between the beta-cyclodextrin and a glucose moiety were synthesized from beta-cyclodextrin and arbutin. They had the significantly high association constants for doxorubicin, the anticancer agent, in the range of 10(5)-10(6) M-1, and worked as highly reactive glycosyl acceptors for the transglycosylation reaction by endo-beta-N-acetylglucosaminidase of Mucor hiemalis to produce sialo-complex type oligosaccharide-branched cyclodextrins in the high yields of 65-67%. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.040