isopropenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside | 139684-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-1-en-2-yloxyoxane
• CAS: 139684-67-6
• 化学式: C₃₇H₄₀O₆
• 分子量: 580.721
• InChiKey: WDFOSQZERHEEHW-KHKVHWIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isopropenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 、 双丙酮半乳糖 在 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以40%的产率得到2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-D-glucopyranosyl-β-(1→6)-1,2 : 3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  The Chemistry of Isopropenyl Glycopyranosides. Transglycosylations and Other Reactions

  摘要：

  Various anomerically pure isopropenyl alpha- and beta-glycopyranosides have been synthesized and shown to undergo synthetically useful transglycosylation reactions with a variety of primary and secondary carbohydrate alcohols. Although stable when stored, isopropenyl glycosides are readily activated as glycosyl donors by a variety of electrophiles, including N-iodosuccinimide/triflic acid, trimethylsilyl triflate, and triflic anhydride. Under conditions that retard formation of the glycosyl cation, the reactivity of isopropenyl glycosides is diverted away from transglycosylation and toward electrophilic addition across the vinyl ether double bond.

  DOI：

  10.1021/jo960190p
• 作为产物：
  描述：

  氯 2,3,4,6-四-O-苄基-|á-D-吡喃葡萄糖苷 、 bis(acetonyl)mercury 以 氯仿 为溶剂， 反应 24.0h， 以85%的产率得到isopropenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  The Chemistry of Isopropenyl Glycopyranosides. Transglycosylations and Other Reactions

  摘要：

  Various anomerically pure isopropenyl alpha- and beta-glycopyranosides have been synthesized and shown to undergo synthetically useful transglycosylation reactions with a variety of primary and secondary carbohydrate alcohols. Although stable when stored, isopropenyl glycosides are readily activated as glycosyl donors by a variety of electrophiles, including N-iodosuccinimide/triflic acid, trimethylsilyl triflate, and triflic anhydride. Under conditions that retard formation of the glycosyl cation, the reactivity of isopropenyl glycosides is diverted away from transglycosylation and toward electrophilic addition across the vinyl ether double bond.

  DOI：

  10.1021/jo960190p

文献信息

• Dually Enzyme- and Acid-Triggered Self-Immolative Ketal Glycoside Nanoparticles for Effective Cancer Prodrug Monotherapy
  作者：Na Yu、Tao Liu、Xi Zhang、Ningqiang Gong、Tianjiao Ji、Jing Chen、Xing-Jie Liang、Daniel S. Kohane、Shutao Guo

  DOI：10.1021/acs.nanolett.0c01973

  日期：2020.7.8

  Amphiphilic glucosyl acetone-based ketal-linked etoposide glycoside prodrug isomers were synthesized and fabricated into excipient-free nanoparticles for effective cancer prodrug monotherapy. Hydrolysis of the glycosidic linkage or the ketal linkage triggered hydrolysis of the other linkage, which resulted in spontaneous self-immolative hydrolysis of the prodrugs. Nanoparticles of the prodrug isomer that

  使用糖苷前药是开发用于化疗的新靶向药物的有前途的策略。但是，体内由于活化不足和缺乏方便的合成方法，阻碍了这种前药的实用性。我们已经开发出了一种合成缩酮缩糖苷前药的创新策略，该缩酮糖苷前药在通过双重酶和酸触发的自消灭机制中被激活是独特的。合成基于两亲葡糖基丙酮的缩酮连接的依托泊苷糖苷前药异构体，并将其制备成不含赋形剂的纳米颗粒，以有效地进行癌症前药单药治疗。糖苷键或缩酮键的水解引发另一个键的水解，这导致前药的自发自焚水解。在溶酶体模拟环境中最不稳定的前药异构体的纳米颗粒在A549异种移植小鼠模型中显示出较高的肿瘤内蓄积和强大的抗肿瘤活性。我们的策略可能对刺激反应性自焚前药及其纳米药物的开发有用。
• Isopropenyl glycosides and congeners as novel classes of glycosyl donors: theme and variations
  作者：Alberto Marra、Jacques Esnault、Alain Veyrieres、Pierre Sinay

  DOI：10.1021/ja00042a010

  日期：1992.7

  Isopropenyl glycosides (i.e., 10 and 11) have been synthesized in high yields by reacting the corresponding anomeric acetates with the Tebbe reagent. These compounds undergo glycosylation with primary or secondary carbohydrate alcohols in the presence of trimethylsilyl triflate or boron trifluoride etherate, probably via a mixed acetal glycoside intermediate. On the basis of this principle, a quite efficient glycosylation of monosaccharide hemiacetal donors (i.e., 1, 7, and 9) with acceptors bearing an isopropenyl ether function at a primary or secondary position (i.e., 18 and 21) has been developed. Also investigated were the glycosylating properties of isopropenyl glucosyl and galactosyl carbonates (i.e., 12-15), easily prepared from the corresponding hemiacetals, toward sugar alcohols. In each case, the beta-selective synthesis of disaccharides from donors having nonparticipating groups at C-2 was ensured by the use of acetonitrile, at low temperature, as the solvent.