heptakis(6-cyano-6-deoxy)cyclomaltoheptaose | 145958-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptakis(6-cyano-6-deoxy)cyclomaltoheptaose
• CAS: 145958-36-7
• 化学式: C₄₉H₆₃N₇O₂₈
• 分子量: 1198.07
• InChiKey: PSWTXJBFSSTWIV-NIVGXQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.78
• 重原子数：
  84.0
• 可旋转键数：
  7.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  578.97
• 氢给体数：
  14.0
• 氢受体数：
  35.0

反应信息

• 作为反应物：
  描述：

  heptakis(6-cyano-6-deoxy)cyclomaltoheptaose 在 platinum(IV) oxide 氢气 作用下， 以 盐酸 为溶剂， 反应 3.0h， 生成 cycloheptakis(1[*]4)-(7-amino-6,7-dideoxy-α-D-gluco-heptopyranosyl)hydrochloride
  参考文献：
  名称：

  Synthesis of Monofacially Functionalized Cyclodextrins Bearing Amino Pendent Groups

  摘要：

  Derivatives of the cyclodextrins, alpha CD, beta CD, and gamma CD, in which all primary hydroxyls are substituted by amine pendant groups, may be synthesized efficiently from the per-6-bromo-6-deoxy-CD derivatives by direct reaction with amines. These ACD derivatives, which bear six, seven! or eight amine pendent groups, represent interesting biomimetic receptors and catalysts. The synthetic strategy relies on quantitative transformation and efficient purification as is demonstrated by preparation of 11 homogeneous ACD derivatives. The limitations of the synthesis and potential adaptations are illustrated by the synthesis of several more ACD derivatives to >95% purity. A synthetic route to a CD persubstituted with primary amine functionalities at the primary face, per-6-(aminomethyl)-6-deoxy-CD, yields an alternative reagent to the simple per-6-amino-6-deoxy-CD, which is more suitable for further synthetic transformations. The synthetic strategy is further adapted to preparation of a prototypical (6 + 1)-ACD derivative in which one primary position is substituted with a sulfide group and the remaining six primary face positions are substituted with amine pendent groups.

  DOI：

  10.1021/jo9711549
• 作为产物：
  描述：

  氰化钠 、 heptakis(6-deoxy-6-iodo)cyclomaltoheptaose 在 Amberlite MB-6113 作用下， 生成 heptakis(6-cyano-6-deoxy)cyclomaltoheptaose
  参考文献：
  名称：

  合成6-（6-氨基-6-脱氧-环麦芽低聚糖）的环己基和环庚基-（1→4）-（7-氨基-6,7-双脱氧-α-D-葡萄糖-七吡喃糖基）。

  摘要：

  DOI：

  10.1016/0008-6215(94)00217-7

文献信息

• Efficient perfacial derivatization of cyclodextrins at the primary face
  作者：Boris I. Gorin、Richard J. Riopelle、Gregory R.J. Thatcher

  DOI：10.1016/0040-4039(96)00916-1

  日期：1996.7

  Synthesis of thirteen cyclodextrin (CD) derivatives via the per-6-bromo-6-deoxy-CD is reported in order to demonstrate the efficiency and ease of perfacial functionalization of α, β and γCD employing a Vilsmeier-Haack reagent.

  为了证明使用Vilsmeier-Haack试剂对α，β和γCD进行表面官能化的效率和易用性，已报道了通过全6-溴6-脱氧CD合成13种环糊精（CD）衍生物。
• Synthesis of a cycloheptaose consisting of (1 → 4)-linked 7-amino-6,7-dideoxy-α-d-gluco-heptopyranosyl units: A new analog of cyclomaltoheptaose
  作者：Hans H. Baer、Yaping Shen、Francisco Santoyo González、Antonio Vargas Berenguel、Joaquin Isac García

  DOI：10.1016/0008-6215(92)80083-d

  日期：1992.11

  Approaches to chain extension al the C-6 positions in cyclomaltoheptaose (1) were examined with the aim of producing novel beta-cyclodextrin analogs composed of heptose or hepturonic acid units. Iron carbonyl-mediated methoxycarbonylation, and nucleophilic displacement by cyanide, in the fully acetylated heptakis(6-deoxy-6-iodo) and heptakis(6-O-mesyl) derivates of 1, respectively, were unsuccessful, as were similar reactions attempted with the newly synthesized, analogous allyl-protected derivatives of 1. However, reaction of unprotected heptakis(6-deoxy-6-iodo)cyclomaltoheptaose with lithium cyanide in N,N-dimethylformamide afforded a high yield of the corresponding heptakis(6-cyano-6-deoxy) compound, namely, cyclohepta-(1 --> 4)-(6-deoxy-alpha-D-gluco-heptopyranosid)urononitrile, catalytic hydrogenation of which gave the title compound, cyclo-(1 --> 4)-(7-amino-6,7-dideoxy-alpha-D-glucoheptopyrano)heptaose, isolated as its peracetyl derivative.