3¹,2²-O-benzylidene-6¹,6²,6³,6⁴,6⁵,6⁶,6⁷-hepta-O-pivaloylcyclomaltoheptaose | 153697-29-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3¹,2²-O-benzylidene-6¹,6²,6³,6⁴,6⁵,6⁶,6⁷-hepta-O-pivaloylcyclomaltoheptaose
• 英文别名: [(1S,3R,5R,6R,7R,11R,12R,14R,15S,17R,19R,20S,22R,24R,25S,27R,29R,30S,32R,34R,35S,37R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R,50S,52R)-5,14,19,24,34,39-hexakis(2,2-dimethylpropanoyloxymethyl)-40,41,42,43,44,45,46,47,48,49,50,52-dodecahydroxy-9-phenyl-2,4,8,10,13,16,18,21,23,26,28,31,33,36,38,51-hexadecaoxanonacyclo[35.2.2.217,20.222,25.227,30.232,35.13,7.16,12.111,15]dopentacontan-29-yl]methyl 2,2-dimethylpropanoate
• CAS: 153697-29-1
• 化学式: C₈₄H₁₃₀O₄₂
• 分子量: 1811.93
• InChiKey: JATVDHVPIXZQHZ-JYJMGMMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  126
• 可旋转键数：
  29
• 环数：
  24.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  575
• 氢给体数：
  12
• 氢受体数：
  42

反应信息

• 作为反应物：
  描述：

  3¹,2²-O-benzylidene-6¹,6²,6³,6⁴,6⁵,6⁶,6⁷-hepta-O-pivaloylcyclomaltoheptaose 、 碘甲烷 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 以89%的产率得到(1R,3R,5R,6R,7S,11R,12R,14R,15R,17R,19R,20R,22R,24R,25R,27R,29R,30R,32R,34R,35R,37R,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R,50S,52R)-40,41,42,43,44,45,46,47,48,49,50,52-dodecamethoxy-5,14,19,24,29,34,39-heptakis(methoxymethyl)-9-phenyl-2,4,8,10,13,16,18,21,23,26,28,31,33,36,38,51-hexadecaoxanonacyclo[35.2.2.217,20.222,25.227,30.232,35.13,7.16,12.111,15]dopentacontane
  参考文献：
  名称：

  Regioselective synthesis of methylated β-cyclodextrins leaving hydroxy groups

  摘要：

  A series of methylated beta -cyclodextrins (CDs) regioselectively leaving one or two hydroxy groups were prepared, and fluorescence spectroscopic measurements showed that they have unique binding characteristics against 2-p-toluidinylnaphthalene-6-sulfonate as a guest molecule in aqueous solution. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02276-0
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 heptakis(6-O-pivaloyl)-β-cyclodextrin 在 (+)-10-camphorsulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 60.0~70.0 ℃ 、2.0 kPa 条件下， 反应 5.0h， 以46%的产率得到3¹,2²-O-benzylidene-6¹,6²,6³,6⁴,6⁵,6⁶,6⁷-hepta-O-pivaloylcyclomaltoheptaose
  参考文献：
  名称：

  Efficient and Regioselective Preparation of an Eight-membered Interglycosidic Benzylidene Derivative of β-Cyclodextrin

  摘要：

  通过 β-环糊精 (β-CD) 新戊酰化以高产率制备庚基 (6-O-新戊酰基)-β-环糊精，在 (+)-10-樟脑磺酸存在下用 α,α-二甲氧基甲苯处理，得到得到八元糖苷间亚苄基缩醛，31,22-O-亚苄基-61,62,63,64,65,66,67-七-O-新戊酰基环麦芽七糖，产率为46%。亚苄基的进一步还原开环反应或酸水解得到了用于 β-CD 区域选择性修饰的多功能中间体。

  DOI：

  10.1246/cl.1993.2077

文献信息

• Regioselective synthesis of methylated β-cyclodextrins leaving hydroxy groups
  作者：Koji Matsuoka、Yoko Shiraishi、Daiyo Terunuma、Hiroyoshi Kuzuhara

  DOI：10.1016/s0040-4039(00)02276-0

  日期：2001.2

  A series of methylated beta -cyclodextrins (CDs) regioselectively leaving one or two hydroxy groups were prepared, and fluorescence spectroscopic measurements showed that they have unique binding characteristics against 2-p-toluidinylnaphthalene-6-sulfonate as a guest molecule in aqueous solution. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Efficient and Regioselective Preparation of an Eight-membered Interglycosidic Benzylidene Derivative of β-Cyclodextrin
  作者：Nobuo Sakairi、Hiroyoshi Kuzuhara

  DOI：10.1246/cl.1993.2077

  日期：1993.12

  Heptakis(6-O-pivaloyl)-β-cyclodextrin, prepared in high yield by pivaloylation of β-cyclodextrin (β-CD), was treated with α,α-dimethoxytoluene in the presence of (+)-10-camphorsulfonic acid to give a 46% yield of eight-membered interglycosidic benzylidene acetal, 31,22-O-benzylidene-61,62,63,64,65,66,67-hepta-O-pivaloylcyclomaltoheptaose. Further reductive ring-opening reaction or acid hydrolysis of the benzylidene group gave versatile intermediates for regioselective modification of β-CD.

  通过 β-环糊精 (β-CD) 新戊酰化以高产率制备庚基 (6-O-新戊酰基)-β-环糊精，在 (+)-10-樟脑磺酸存在下用 α,α-二甲氧基甲苯处理，得到得到八元糖苷间亚苄基缩醛，31,22-O-亚苄基-61,62,63,64,65,66,67-七-O-新戊酰基环麦芽七糖，产率为46%。亚苄基的进一步还原开环反应或酸水解得到了用于 β-CD 区域选择性修饰的多功能中间体。