6¹,6³-di-O-(tert-butyldimethylsilyl)-β-CD | 130925-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6¹,6³-di-O-(tert-butyldimethylsilyl)-β-CD
• 英文别名: 6¹,6³-bis-O-(tert-butyldimethylsilyl)-β-cyclodextrin；(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)-5,15-bis[[tert-butyl(dimethyl)silyl]oxymethyl]-10,20,25,30,35-pentakis(hydroxymethyl)-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
• CAS: 130925-48-3
• 化学式: C₅₄H₉₈O₃₅Si₂
• 分子量: 1363.52
• InChiKey: BDPUEQZOZHOJID-RECQWNEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.17
• 重原子数：
  91.0
• 可旋转键数：
  11.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  532.05
• 氢给体数：
  19.0
• 氢受体数：
  35.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 6¹,6³-di-O-(tert-butyldimethylsilyl)-β-CD 在 吡啶 、 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 7.0h， 以94.6%的产率得到[(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecaacetyloxy-15,20,25,30-tetrakis(acetyloxymethyl)-10,35-bis(hydroxymethyl)-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]nonatetracontan-5-yl]methyl acetate
  参考文献：
  名称：

  Preparation and characterization of 6I,6n-di-O-(l-fucopyranosyl)-β-cyclodextrin (n=II–IV) and investigation of their functions

  摘要：

  Three positional isomers of 6(I),6(n)-di-O-(beta-L-fucopyranosyl)-cyclomaltoheptaose [61,6(n)-di-O-(beta-L-Fuc)-beta-cyclodextrin, -beta CD, n = II-IV] were chemically synthesized using the corresponding authentic compounds, 6(I),6(n)-di-O-(tert-butyidimethylsilyl)-beta CD (n = II-IV), as the fucosyl acceptors, and 2,3,4-tri-O-acetyl-L-fucopyranosyl trichloroacetimidate as the fucosyl donor. Their structures were analyzed by HPLC, MS, and NMR spectroscopy. The hemolytic activities of L-Fuc-beta CDs were lower than that of beta CD, while the solubilities of these branched CDs in water were much higher than that of beta CD. The molecular interaction between these compounds and the fucose-binding lectin Aleuria aurantia lectin (AAL) was investigated using an optical biosensor based on a surface plasmon resonance (SPR) technique. The order of binding affinity, as a function of the fucose-binding position, was 6(I),6(IV)- 6(I),6(III)- > 6(I),6(II)-di-O-(beta-L-Fuc)-beta CD > 6-O-(beta-L-Fuc)-beta CD. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.06.016
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 β-环糊精 在 吡啶 作用下， 生成 6¹,6²-di-O-(tert-butyldimethylsilyl)-β-CD 、 6¹,6⁴-di-O-(tert-butyldimethylsilyl)-β-CD 、 6¹,6³-di-O-(tert-butyldimethylsilyl)-β-CD
  参考文献：
  名称：

  聚合度（dp）= 9的支化环麦芽七糖（βCD）的五个异构体的表征：对二葡糖基-βCD的三个位置异构体进行重新研究。

  摘要：

  通过甲基化分析和化学合成已证实，从带有大芽孢杆菌环麦芽糖糊精葡聚糖转移酶的大规模制备β-CD的母液中分离出的支链环麦芽七糖（βCD）的三个异构体是6（1），6（4）-二-O-（α-D-吡喃葡萄糖基）-环麦芽庚糖（1），6（1），6（3）-二-O-（α-D-吡喃葡萄糖基）-环麦芽庚糖（2）和6-O- α-异麦芽糖基）-环麦芽庚糖（4）代替了6（1），6（2）-二-O-（α-D-吡喃葡萄糖基）-麦芽七糖（3），这在先前的论文中被错误地描述了。已经从通过用葡糖淀粉酶的逆作用由麦芽糖和βCD合成的麦芽糖β-CD混合物的葡糖淀粉酶水解制备的葡糖基-βCD混合物中新分离了化合物3。色谱行为和光谱数据（13C-nmr和fa

  DOI：

  10.1016/0008-6215(91)84013-5

文献信息

• Polysulfonylated cyclodextrins. Part 11. Preparation and structural validation of three isomeric pentakis(6-O-mesitylsulfonyl)cyclomaltoheptaoses †
  作者：Hatsuo Yamamura、Daisuke Iida、Shuki Araki、Kyoko Kobayashi、Ryoichi Katakai、Kazuaki Kano、Masao Kawai

  DOI：10.1039/a906436b

  日期：——

  Three isomers of cyclomaltoheptaose derivatives, 1a–c, which possess five mesitylenesulfonyloxy groups on their C-6 atoms, were prepared. Assignment of the regiosiomers was performed by their conversion into compounds containing five 3,6-anhydroglucose units followed by 1H NMR analyses. The structures of the pentakis(3,6-anhydro) derivatives were also confirmed by their derivation from the known bis(TBDMS) derivatives.

  我们制备了环庚糖衍生物的三种异构体 1aâc，它们的 C-6 原子上具有五个间苯磺酰氧基。通过将其转化为含有五个 3,6-anhydroglucose 单元的化合物，然后进行 1H NMR 分析，从而确定了这些异构体。五(3,6-脱水)衍生物的结构也通过从已知的双(TBDMS)衍生物衍生得到证实。
• Nakanishi, Noriko; Saeki, Mitsuyo; Koizumi, Kyoko, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 6, p. 923 - 934
  作者：Nakanishi, Noriko、Saeki, Mitsuyo、Koizumi, Kyoko

  DOI：——

  日期：——
• NAKANISHI, NORIKO;TSUJIKAWA, JUNKO;HARA, NAOMI;TANIMOTO, TOSHIKO;KOIZUMI,+, YAKUGAKU DZASSI, 110,(1990) N, S. 477-483
  作者：NAKANISHI, NORIKO、TSUJIKAWA, JUNKO、HARA, NAOMI、TANIMOTO, TOSHIKO、KOIZUMI,+

  DOI：——

  日期：——