1-O-isopropyl-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose | 40593-02-0

• 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: 1-O-isopropyl-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose
• 英文别名: isopropyl-3,4,6-tri-O-acetate-2-deoxy-α-D-glucopyranoside；isopropyl-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside；i-propyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside；isopropyl 3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranoside
• CAS: 40593-02-0
• 化学式: C₁₅H₂₄O₈
• 分子量: 332.351
• InChiKey: PWRYPBFZDBKFLP-KBXIAJHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 三甲基溴硅烷 、 氢溴酸 、 溶剂黄146 、 三苯基氧化膦 作用下， 以 二氯甲烷 为溶剂， -15.0~20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 1-O-isopropyl-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose 、 isopropyl 3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranoside
  参考文献：
  名称：

  TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

  摘要：

  甘露糖醛酸盐的硫加成反应可以在无溶剂条件下高效地通过等物量的溴化三甲基硅(TMSBr)催化产生良好至优异收率的S-2-脱氧糖苷。此外，加入三苯基膦氧化物作为添加剂，TMSBr介导的甘露糖醛酸盐与多种醇类的直接糖基化反应具有高度α-选择性。

  DOI：

  10.3762/bjoc.12.164

文献信息

• Additive‐Free Gold(III)‐Catalyzed Stereoselective Synthesis of 2‐Deoxyglycosides Using Phenylpropiolate Glycosides as Donors
  作者：Mukta Shaw、Amit Kumar

  DOI：10.1002/asia.201900888

  日期：2019.12.13

  Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields

  在无外部添加剂的条件下，使用金（III）盐作为催化剂，可从台式稳定且易于合成的脱氧苯丙酸丙二醇酯（D-PPGs）中实现脱氧糖苷的立体选择性合成。在简单的催化系统下，D-PPG与多种糖和非糖受体反应，以高至优异的收率产生主要的α-立体选择性O / N-脱氧糖苷，并再生易于分离和重用的苯丙酸。在优化的反应条件下，含有武装和解除武装团体的脱氧PPG能够很好地存活。另外，展示了D-PPG的正交性质，并且还合成了1，1'-连接的海藻糖型糖。
• Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation
  作者：Titli Ghosh、Ananya Mukherji、Hemant Kumar Srivastava、Pavan K. Kancharla

  DOI：10.1039/c8ob00423d

  日期：——

  A new organocatalytic glycosylation method exploiting the lactol functionality has been disclosed. The catalytic generation of glycosyl oxacarbenium ions from lactols under forcible conditions via weakly Brønsted-acidic, readily available secondary amine salts affects the diastereoselective glycosylation of 2-deoxypyranoses and furanoses. This operationally simple iminium catalyzed activation of 2-deoxy

  已经公开了利用乳醇官能度的新的有机催化糖基化方法。在强力条件下，通过弱布朗斯台德酸，容易获得的仲胺盐，在强迫条件下由乳糖醇催化生成糖基氧杂碳鎓离子会影响2-脱氧吡喃糖和呋喃糖的非对映选择性糖基化。这种操作简单的亚胺基催化的2-脱氧半缩醛的活化是需要特殊处理的现有繁琐方法的潜在替代方法。基于实验证据和理论研究，已经讨论了这种独特转化和动力学/热力学效应的机理。
• α-Selective synthesis of 2-deoxy-glycosides and disaccharides
  作者：Guofang Yang、Xiaosheng Luo、Hong Guo、Qingbing Wang、Jiafen Zhou、Tianyun Huang、Jie Tang、Junjie Shan、Jianbo Zhang

  DOI：10.1080/07328303.2018.1439498

  日期：2018.3.24

  A metal-free catalytic method for the synthesis of 2-deoxy glycosides and disaccharides has been developed using stable 2-deoxy glucosyl and galactosyl acetate donors. They could react with a variety of acceptors in the presence of catalytic amount of TMSOTf at 0 degrees C to form glycosides, glycoconjugates, and disaccharides with excellent alpha-selectivity (> 19:1) and yields (up to 99%) in a short time (0.5 h). With this expedient method, several new compounds against human K562 and SMMC7721 cell lines were obtained and tested with in vitro antitumor bioactivities.
• Fluorine-Directed Glycosylation
  作者：Christoph Bucher、Ryan Gilmour

  DOI：10.1002/anie.201004467

  日期：2010.11.8