n-propyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside | 85618-23-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: n-propyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-propylsulfanyloxan-2-yl]methyl acetate
• CAS: 85618-23-1
• 化学式: C₁₇H₂₆O₉S
• 分子量: 406.454
• InChiKey: GHQYCDJTLYWURK-UUAJXVIYSA-N

物化性质

• 熔点：
  83.2-84.1 °C
• 沸点：
  465.8±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  n-propyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 camphor-10-sulfonic acid 、 copper(II) bis(trifluoromethanesulfonate) 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 40.3h， 生成 propyl 2,3-di-O-benzoyl-4-O-benzyl-6-O-levulinyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  手动工艺向机器辅助合成转化的挑战：芳基（三氟乙基）碘化三氟甲磺酸酯激活硫代糖苷供体

  摘要：

  描述了使稳定的碘鎓促进剂适用于自动化的氟辅助溶液相低聚糖合成所需的步骤。最初报道的分批方法的直接适应导致原酸酯或保护基转移至糖基受体的形成。幸运的是，添加廉价的β-pine烯作为除酸剂避免了这两个副反应。此新开发的协议的实用程序应用于β-葡聚糖片段的自动溶液相合成。

  DOI：

  10.1021/acs.orglett.7b03940
• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-glucopyranose 在 Molekularsieb 4 A 、 三氟化硼乙醚 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成 n-propyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Schmidt, Richard R.; Stumpp, Michael, Liebigs Annalen der Chemie, 1983, # 7, p. 1249 - 1256

  摘要：

  DOI：

文献信息

• Pentavalent Bismuth as a Universal Promoter for S-Containing Glycosyl Donors with a Thiol Additive
  作者：Daniel E. K. Kabotso、Nicola L. B. Pohl

  DOI：10.1021/acs.orglett.7b02080

  日期：2017.9.1

  S-Propyl glycosides of less activated sugars, such as peracetylated carbohydrates and uronic acid esters that could not previously be activated with triphenylbismuth ditriflate alone, were found to be glycosylated in the presence of propanethiol as an additive in under 3 h. This newly developed protocol was also found to be effective in promoting glycosylation of neutral and uronic acid esters of S-phenyl

  发现在三小时内在丙硫醇作为添加剂存在下，活化程度较低的糖（例如过乙酰化的碳水化合物和糖醛酸酯类）的S-丙基糖苷以前无法单独用三苯基铋三氟甲磺酸酯活化，因此被糖基化。还发现该新开发的方案可有效促进S-苯基，S-噻唑啉基，S-苯并恶唑基和S-金刚烷基糖苷以及唾液酸的中性和糖醛酸酯的糖基化。
• Bismuth(V)-Mediated Thioglycoside Activation
  作者：Manibarsha Goswami、Arkady Ellern、Nicola L. B. Pohl

  DOI：10.1002/anie.201304099

  日期：2013.8.5

  A straightforward method utilizing a bismuth(V) compound was developed for the activation of thiopropylglycosides for coupling to various acceptors; good to excellent yields were obtained without applying additional additives/co‐promoters. The method does not require low temperatures, is applicable to a wide variety of carbohydrates, and tolerates different functional groups including alkenes.

  开发了一种简单的利用铋（V）化合物的方法来激活硫丙基丙基糖苷以偶联到各种受体上。在不使用其他添加剂/助促进剂的情况下获得了良好至极好的收率。该方法不需要低温，适用于多种碳水化合物，并且可以耐受包括烯烃在内的不同官能团。
• Synthesis and liquid crystalline properties of the n-alkyl 1-thio-α-d-glucopyranosides, a new homologous series of carbohydrate mesogens
  作者：Henk A. van Doren、Ralph van der Geest、Richard M. Kellogg、Hans Wynberg

  DOI：10.1016/0008-6215(89)85007-4

  日期：1989.12

  deacetylation. The n -propyl and n -butyl derivatives are not thermotropic, the n -pentyl derivative is monotropic, and the compounds with n -hexyl and longer alkyl chains are enantiotropic, the largest liquid crystalline range being from ±100–175° for the n -undecyl derivative. The transition point data are typical for smectic behavior, and X-ray data and texture observations are indicative of a smectic A d phase

  摘要用1,2,3,4,6-五戊-O-乙酰基-β-d-吡喃葡萄糖处理1,2,3,4,6-戊-O-乙酰基-β-d-吡喃葡萄糖制备了n-烷基1-硫代-α-d-吡喃葡萄糖苷（正丙基至正十二烷基）。在三氟化硼醚化物的存在下链烷硫醇，然后脱乙酰化。正丙基和正丁基衍生物不是热致性的，正戊基衍生物是单亲的，具有正己基和较长烷基链的化合物是对映体的，n的最大液晶范围为±100–175° -十一烷基衍生物。转变点数据是近晶行为的典型特征，X射线数据和纹理观察表明近晶A d相。
• Involvement of the S-aglycon in the conformational preferences of thioglucosides
  作者：Carlos A. Sanhueza、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.tetasy.2008.01.003

  日期：2008.2

  The conformational preferences of two series of alkyl beta-D-thioglucopyranosides in solution were investigated by NMR and CD. The rotamer populations of the hydroxymethyl group were found to depend on the structural nature of the S-aglycon. The population of the gt rotamer increased and that of the gg rotamer decreased as the alkyl group attached to the S atom increased in size. These rotamer populations have a linear correlation with the Taft' steric parameters, the n(S)-sigma(C-O)* exo-anomeric interaction may express these rotational preferences. Comparative analysis of the hydroxymethyl populations between alkyl O- and S-glucosides revealed identical or slightly higher gt and smaller gg populations for the latter compounds. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of O- and S-glucosides using glucosyl halides and zinc salts
  作者：K Gurudutt

  DOI：10.1016/0008-6215(96)00011-0

  日期：1996.5.14