(2S,3R,4S,5R,6R)-2-[4-(3-iodopropoxy)phenoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane | 848940-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-2-[4-(3-iodopropoxy)phenoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 848940-07-8
• 化学式: C₄₃H₄₅IO₇
• 分子量: 800.731
• InChiKey: WSCSZTLXQWUFQA-BQLIBBPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2^A,2^B,2^C,2^D,2^E,2^F,2^G,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^B,6^C,6^D,6^E,6^F,6^G-eicosa-O-benzyl-β-cyclodextrin 、 (2S,3R,4S,5R,6R)-2-[4-(3-iodopropoxy)phenoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane 在 palladium dihydroxide 氢氧化钾 、 氢气 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 、 乙醚 、 水 为溶剂， 反应 48.0h， 生成 (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,30,35-hexakis(hydroxymethyl)-25-[3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]propoxymethyl]-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
  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：

  熊果苷 在 吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 150.5h， 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

文献信息

• Synthesis of mono-glucose-branched cyclodextrins with a high inclusion ability for doxorubicin and their efficient glycosylation using Mucor hiemalis endo-β-N-acetylglucosaminidase
  作者：Takashi Yamanoi、Naomichi Yoshida、Yoshiki Oda、Eri Akaike、Maki Tsutsumida、Natsumi Kobayashi、Kenji Osumi、Kenji Yamamoto、Kiyotaka Fujita、Keiko Takahashi、Kenjiro Hattori

  DOI：10.1016/j.bmcl.2004.12.040

  日期：2005.2

  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.