2,3,4,6-tetra-O-tert-butyldimethylsilyl-D-galactono-1,5-lactone | 318967-96-3

• 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-tert-butyldimethylsilyl-D-galactono-1,5-lactone
• 英文别名: (3R,4S,5S,6R)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(dimethyl)silyl]oxymethyl]oxan-2-one
• CAS: 318967-96-3
• 化学式: C₃₀H₆₆O₆Si₄
• 分子量: 635.192
• InChiKey: LERUUIRSJOIJKL-WSOYEBOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-tert-butyldimethylsilyl-D-galactono-1,5-lactone 在 四丁基氟化铵 、 三氟乙酸 作用下， 以 吡啶 为溶剂， 生成 (2R,3R,4S,5R,6Z)-2-(hydroxymethyl)-6-prop-2-enylideneoxane-3,4,5-triol
  参考文献：
  名称：

  从糖内酯快速合成C-糖基共轭二烯和醛

  摘要：

  通过添加烯丙基氯化镁并随后进行脱水，由受保护的糖内酯分两步制备几种C-糖基共轭二烯。一系列烯丙基加成，臭氧分解和脱水导致相应的糖基缀合的醛。这些共轭的功能可以用作糖合成和纯化的诊断生色团。还进行了糖基二烯的合成研究。糖二烯的氢硼化取决于后处理条件而导致均一醇或螺缩醛。

  DOI：

  10.1016/s0040-4039(01)00814-0
• 作为产物：
  描述：

  苄基alpha-D-吡喃半乳糖苷 在 吡啶 、 pyridinium chlorochromate 作用下， 生成 2,3,4,6-tetra-O-tert-butyldimethylsilyl-D-galactono-1,5-lactone
  参考文献：
  名称：

  Yang; Yang; Teo, Synlett, 2000, # 11, p. 1634 - 1636

  摘要：

  DOI：

文献信息

• Synthesis of Three <i>C</i> ‐Glycoside Analogues of UDP‐Galactopyranose as Conformational Probes for the Mutase‐Catalyzed Furanose/Pyranose Interconversion
  作者：Audrey Caravano、Stéphane P. Vincent

  DOI：10.1002/ejoc.200801249

  日期：2009.4

  AbstractUDP‐galactopyranose mutase (UGM) catalyzes the isomerization of UDP‐galactopyranose (UDP‐Galp) into UDP‐galactofuranose (UDP‐Galf), an essential step of the mycobacterial cell wall biosynthesis. In order to probe the UGM binding pocket, we synthesized the α‐ and β‐C‐glycosidic analogues of UDP‐galacopyranose along with the corresponding UDP‐exo‐galactal. Preliminary inhibition evaluation indicated that UDP‐exo‐galactal inhibits UGM with a binding affinity similar to that of UDP‐α‐C‐galactopyranose.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Divergent Synthesis ofL-Sugars andL-Iminosugars fromD-Sugars
  作者：Hideyo Takahashi、Tomomi Shida、Yuko Hitomi、Yoshinori Iwai、Namisa Miyama、Kazusa Nishiyama、Daisuke Sawada、Shiro Ikegami

  DOI：10.1002/chem.200600268

  日期：2006.7.24

  AbstractAn efficient divergent synthesis of L‐sugars and L‐iminosugars from D‐sugars is described. The important intermediate, δ‐hydroxyalkoxamate, prepared from D‐glucono‐/galactono‐1,5‐lactone, was cyclized under Mitsunobu conditions to give the O‐cyclized oxime compound and the N‐cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O‐/N‐cyclization of the δ‐hydroxyalkoxamate. Suitable protection at the 6‐position of δ‐hydroxyalkoxamate, derived from D‐glucono‐1,5‐lactone, afforded the corresponding O‐alkylation product alone. Thus we succeeded in applying this to the total synthesis of L‐iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of D‐glucono/galactono‐1,5‐lactone into the corresponding L‐iminosugars (L‐idonolactam and L‐altronolactam) was achieved.