2,3,4,6-tetra-O-t-butyldimethylsilyl-D-glucono-1,5-lactone | 157461-21-7

• 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-t-butyldimethylsilyl-D-glucono-1,5-lactone
• 英文别名: tetra-O-t-butyldimethylsilyl-D-glucono-1,5-lactone；(3R,4S,5R,6R)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(dimethyl)silyl]oxymethyl]oxan-2-one
• CAS: 157461-21-7
• 化学式: C₃₀H₆₆O₆Si₄
• 分子量: 635.192
• InChiKey: LERUUIRSJOIJKL-ZKGSSEMHSA-N

物化性质

• 沸点：
  546.6±50.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

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-t-butyldimethylsilyl-D-glucono-1,5-lactone 在 三氯化硼 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 为溶剂， 反应 0.2h， 生成 (2S,3R,4S,5R)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-carbaldehyde
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 葡萄糖酸内酯 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,3,4,6-tetra-O-t-butyldimethylsilyl-D-glucono-1,5-lactone
  参考文献：
  名称：

  PdII催化的酮基烯丙基二元醇的螺环化

  摘要：

  报道了一种由简单的酮基烯丙基二醇形成螺环酮的高产立体选择性方法。这些脱水环化反应通过在0°C下于THF中使用催化[PdCl 2（MeCN）2 ]进行，仅需温和的条件即可在短暂的水反应时间后，以高收率生产乙烯基取代的螺酮金属。使用这种方法，亲核试剂中嵌入的立体化学信息会“向下传递”，并有效地在异头碳原子和新形成的烯丙基立体中心设置立体化学。

  DOI：

  10.1002/chem.201301723

文献信息

• Expeditious synthesis of C-glycosyl conjugated dienes and aldehydes from sugar lactones
  作者：Wen-Bin Yang、Chuan-Fa Chang、Shwu-Huey Wang、Chin-Fen Teo、Chun-Hung Lin

  DOI：10.1016/s0040-4039(01)00814-0

  日期：2001.7

  Several C-glycosyl conjugated dienes were prepared in two steps from protected sugar lactones via addition of allylmagnesium chloride and the subsequent dehydration. A sequence of allylic addition, ozonolysis and dehydration led to the corresponding glycosyl conjugated aldehydes. These conjugated functionalities can be used as diagnostic chromophores for sugar synthesis and purification. The synthetic

  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。
• 一种1-C-取代苯基吡喃葡萄糖碳苷的制备方法
  申请人：浙江宏元药业股份有限公司

  公开号：CN116120299A

  公开（公告）日：2023-05-16

  本发明提供了一种1‑C‑[4‑氯‑3‑[[4‑[[(3S)‑四氢‑3‑呋喃基]氧基]苯基]甲基]苯基]‑D‑葡萄糖碳苷和1‑C‑[4‑氯‑3‑[[4‑乙氧基]苯基]甲基]苯基]‑D‑葡萄糖碳苷的制备方法。本发明所述的制备方法，相对于现有技术，其突出实质性特征为碳苷化反应过程中加入了有机胺类物质。有机胺类物质能显著改善碳苷化反应的效果，提高了碳苷化反应的立体选择性，大大降低特征杂质的生成，提高目标产物的分离收率和质量，具有显著的进步。制备方法操作简便，对恩格列净、达格列净等产品的产业化具有重要的意义。
• Collins, David J.; Jones, Eric D., Australian Journal of Chemistry, 1994, vol. 47, # 7, p. 1419 - 1422
  作者：Collins, David J.、Jones, Eric D.

  DOI：——

  日期：——
• 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.
• Enzymes in organic synthesis: oxidoreductions
  作者：Jim-Min Fang、Chun-Hung Lin、Curt W. Bradshaw、Chi-Huey Wong

  DOI：10.1039/p19950000967

  日期：——

  This article reviews the use of several oxidoreduction enzymes, including monooxygenases, chloroperoxidase, arene dioxygenase, lipoxygenase, galactose oxidase and alcohol dehydrogenases, in the preparation of optically pure or enriched epoxides, halohydrins, sulfoxides, hydroperoxides, alcohols, cyclohexadienediols, lactones and alpha-hydroxy aldehydes. The mechanisms of some of these enzyme-catalysed transformations, and their scopes and limitations in synthetic chemistry are also discussed. Representative syntheses of a key intermediate of 5-lipoxygenase inhibitor, a seven-carbon C-glycoside and an active component of the antibiotic bialaphos have been experimentally illustrated using Lactobacillus alcohol dehydrogenase, chloroperoxidase and glutamate dehydrogenase, respectively.