2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate | 127066-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate
• 英文别名: β-thiocyanato-tetraacetyl-glucopyranoside；tetra-O-acetyl-β-D-glucopyranosyl thiocyanate；Tetra-O-acetyl-β-D-glucopyranosylthiocyanat；2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosylthiocyanat；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-thiocyanatooxan-2-yl]methyl acetate
• CAS: 127066-70-0
• 化学式: C₁₅H₁₉NO₉S
• 分子量: 389.383
• InChiKey: QTQCVHQWXQCSCO-QMIVOQANSA-N

物化性质

• 熔点：
  132 °C
• 沸点：
  477.1±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  164
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate 生成 O-ethyl N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamate
  参考文献：
  名称：

  Mueller; Wilhelms, Chemische Berichte, 1941, vol. 74, p. 698,700

  摘要：

  DOI：
• 作为产物：
  描述：

  1-硫代-b-D-葡萄糖四乙酸酯 、 3-氧代-1,2-苯并碘氧戊环-1(3H)-甲腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以95%的产率得到2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate
  参考文献：
  名称：

  从硫醇中硫氰酸盐的一般和实际形成

  摘要：

  描述了一种使用氰基苯并齐多醇（on）高价碘试剂氰化硫醇和二硫化物的新方法。脂肪族和芳香族硫氰酸酯都可以在室温下以几分钟的高收率获得，其起始源是多种具有高化学选择性的硫醇。也可以将二硫化物完全转化为硫氰酸酯。初步的计算研究表明，硫氰酸根阴离子或自由基的氰化反应具有低能的一致过渡态。发达的硫氰酸酯合成方法在合成化学，化学生物学和材料科学中具有广泛的应用潜力。

  DOI：

  10.1002/chem.201406171

文献信息

• Method of heightening optical purity of 1-benzyl-3-aminopyrrolidine and salt for used therein
  申请人：——

  公开号：US20040249169A1

  公开（公告）日：2004-12-09

  The present invention provides a method to improve the optical purity of 1-benzyl-3-aminopyrrolidine having a low optical purity using an inexpensive agent via a simple procedure. The present invention provides a method for improving the optical purity of 1-benzyl-3-aminopyrrolidine including the steps of converting 1-benzyl-3-aminopyrrolidine into an equimolar salt with an optically inactive acid, and recovering the salt as crystals. The present invention also provides a salt of 1-benzyl-3-aminopyrrolidine that is used in the method.

  本发明提供了一种方法，通过简单的程序利用廉价试剂提高具有低光学纯度的1-苄基-3-氨基吡咯啉的光学纯度。本发明提供了一种改善1-苄基-3-氨基吡咯啉的光学纯度的方法，包括将1-苄基-3-氨基吡咯啉转化为与光学不活性酸的等摩尔盐，并将盐回收为晶体。本发明还提供了用于该方法的1-苄基-3-氨基吡咯啉的盐。
• Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides.
  作者：Zbigniew Pakulski、Donat Pierożyński、Aleksander Zamojski

  DOI：10.1016/s0040-4020(01)87009-5

  日期：1994.2

  Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at −40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading

  在-40℃下，具有被乙酰基或苯甲酰基保护的羟基的糖基硫氰酸氰酸酯易于与格氏试剂反应，以高收率得到相应的烷基或芳基硫代糖苷。在相似条件下形成在其他位置具有SCN基团的单糖衍生物可形成硫醚。轴向硫氰酸盐不反应。升高的温度引起副反应，导致硫醇。
• The Michaelis–Arbuzov rearrangement of anomeric thiocyanates: synthesis and application of S-glycosyl thiophosphates, thiophosphonates and thiophosphinates as glycosyl donors
  作者：Marta Piekutowska、Zbigniew Pakulski

  DOI：10.1016/j.tetlet.2007.09.162

  日期：2007.11

  Reaction of anomeric thiocyanates with triethyl phosphite, dimethyl phenylphosphonite and methyl diphenylphosphinite afforded the corresponding S-glycosyl thiophosphates, thiophosphonates and thiophosphinates in good yields. These derivatives were applied as glycosyl donors in the synthesis of benzyl glycosides and disaccharides with excellent stereoselectivity.

  异头硫氰酸酯与亚磷酸三乙酯，二甲基苯基膦酸酯和甲基二苯基次膦酸酯的反应以良好的产率得到了相应的S-糖基硫代磷酸酯，硫代膦酸酯和硫代膦酸酯。这些衍生物被用作糖基供体，以优异的立体选择性合成苄基糖苷和二糖。
• Method for improving optical purity of 1-benzyl-3-aminopyrolidine and salt for use therein
  申请人：Kano Fumihiko

  公开号：US20080255371A1

  公开（公告）日：2008-10-16

  The present invention provides a method to improve the optical purity of 1-benzyl-3-aminopyrrolidine having a low optical purity using an inexpensive agent via a simple procedure. The present invention provides a method for improving the optical purity of 1-benzyl-3-aminopyrrolidine including the steps of converting 1-benzyl-3-aminopyrrolidine into an equimolar salt with an optically inactive acid, and recovering the salt as crystals. The present invention also provides a salt of 1-benzyl-3-aminopyrrolidine that is used in the method.

  本发明提供了一种方法，通过简单的程序使用廉价试剂来提高光学纯度低的1-苄基-3-氨基吡咯烷的光学纯度。本发明提供了一种改善1-苄基-3-氨基吡咯烷光学纯度的方法，包括将1-苄基-3-氨基吡咯烷转化为与光学无活性酸的等摩尔盐，并以晶体形式回收盐。本发明还提供了用于该方法的1-苄基-3-氨基吡咯烷盐。
• A new stereospecific method for 1,2-cis-glycosylation
  作者：Nicolay K. Kochetkov、Evgeny M. Klimov、Nelly N. Malysheva、Alexey V. Demchenko

  DOI：10.1016/0008-6215(91)84047-i

  日期：1991.6

  A new stereospecific method for 1,2-cis-glycosylation involves the reaction of 1,2-trans-glycosyl thiocyanates with sugar trityl ethers in the presence of triphenylmethylium perchlorate, The method has been applied to give disaccharide derivatives with (1 --> 6), (1 --> 4),(1 --> 3), and (1 --> 2) linkages.