benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside | 55692-90-5

• 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: benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(benzylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate；Benzyl-2,3,4,6-tetra-O-acetyl-β-D-thio-galaktopyranosid；benzyl-(tetra-O-acetyl-1-thio-β-D-galactopyranoside)；Benzyl-(tetra-O-acetyl-1-thio-β-D-galactopyranosid)；I(2)-D-Galactopyranoside, phenylmethyl 1-thio-, 2,3,4,6-tetraacetate；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-benzylsulfanyloxan-2-yl]methyl acetate
• CAS: 55692-90-5
• 化学式: C₂₁H₂₆O₉S
• 分子量: 454.498
• InChiKey: UVVCYZREUQWNFB-IFLJBQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 benzyl β-D-thiogalactopyranoside
  参考文献：
  名称：

  走向动态药物设计：动态半硫缩醛系统中β-半乳糖苷酶抑制剂的鉴定和优化

  摘要：

  一种发现策略依赖于通过构造动态系统的解析来鉴定片段，再进行后续的静态配体设计和优化，从而产生了一系列β-半乳糖苷酶抑制剂。抑制研究为这些化合物提供了重要的结构信息，其中1-硫代苄基-β - D-吡喃半乳糖苷显示出最佳的抑制作用。

  DOI：

  10.1002/cbic.201000158
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.25h， 生成 benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates

  摘要：

  三异丙基硅硫代糖苷（TIPS S-糖苷）可以从糖基卤化物、糖基醋酸酯或对甲氧苯基糖苷中轻松合成，一锅法中可以高产率、短时间内去硅基并进行S-烷基化、酰化或糖基化。

  DOI：

  10.1039/c4ob00741g

文献信息

• Modified One‐Pot Protocol for the Preparation of Thioglycosides from Unprotected Aldoses via <i>S</i>‐Glycosyl Isothiouronium Salts
  作者：Pallavi Tiwari、Geetanjali Agnihotri、Anup Kumar Misra

  DOI：10.1080/07328300500256775

  日期：2005.9.1

  An efficient one‐pot protocol for the direct preparation of thioglycosides starting from unprotected reducing sugars via S‐glycosyl isothiouronium salts is reported. In this one‐pot methodology, BF3 · OEt2 has been used as a general catalyst for both per‐O‐acetylation of sugars and conversion of sugar per‐O‐acetates into S‐glycosyl isothiouronium salts, which was allowed to react with alkylating agents

  据报道，一种有效的一锅法方案可直接从未保护的还原糖开始，通过S-糖基异硫脲盐直接制备硫糖苷。在这种一锅法中，BF3·OEt2已被用作糖的全O-乙酰化和糖的过O-乙酸转化为S-糖基异硫脲盐的通用催化剂，该盐可与烷化剂反应在碱的存在下以优异的产率提供硫代糖苷。* CDRI通讯号 6767.作者对这项工作做出了同等的贡献。
• 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。
• Synthesis of thio- and selenoglycosides by cleavage of dichalconides in the presence of zinc/zinc chloride and reaction with glycosyl bromides
  作者：Chinmoy Mukherjee、Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.tetlet.2005.11.074

  日期：2006.1

  A convenient odorless methodology has been devised for the preparation of 1,2-trans-thio- and selenoglycosides through zinc-mediated cleavage of disulfides and diselenides and reaction of the thiolate and selenides formed in situ with glycosyl bromides. The yields were excellent in all cases.

  已经设计了一种方便的无味方法，用于通过锌介导的二硫化物和二硒化物的裂解以及原位形成的硫醇盐和硒化物与糖基溴化物的反应来制备1,2-反式-硫代和硒代糖苷。在所有情况下，收率都非常好。
• Stereoselective Synthesis of β-Glycosyl Thiols and Their Synthetic Applications
  作者：Manas Jana、Anup Kumar Misra

  DOI：10.1021/jo302115k

  日期：2013.3.15

  A significantly fast reaction condition for the exclusive preparation beta-glycosyl thiol derivatives has been developed successfully. The reaction condition is one-step, fast, high yielding, highly stereoselective, and requires only benchtop chemicals. Further reaction of glycosyl thiol derivatives with Michael acceptors and alkylating agents furnished thioglycosides and (1,1)-thiolinked trehalose analogs.
• Bogusiak, Jadwiga; Szeja, Wieslaw, Polish Journal of Chemistry, 1985, vol. 59, # 3, p. 293 - 298
  作者：Bogusiak, Jadwiga、Szeja, Wieslaw

  DOI：——

  日期：——