1-O-((S)-6-methoxy-α-methyl-2-naphthaleneacetyl)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-((S)-6-methoxy-α-methyl-2-naphthaleneacetyl)-β-D-glucopyranoside
• 英文别名: 1-O-{(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl}-β-D-glucopyranoside；(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl (S)-2-(6-methoxynaphthalen-2-yl)propanoate；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
• 化学式: C₂₀H₂₄O₈
• 分子量: 392.406
• InChiKey: ZHVBXKZVLXPWNQ-UPVJBQKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  萘普生 生成 1-O-((S)-6-methoxy-α-methyl-2-naphthaleneacetyl)-β-D-glucopyranoside
  参考文献：
  名称：

  USHIYAMA, MASASHI;ASADA, YOSHIHISA;YOSHIKAWA, TAKAFUMI;FURUYA, TSUTOMU, PHYTOCHEMISTRY, 28,(1989) N, C. 1859-1869

  摘要：

  DOI：

文献信息

• An Improved Chemo-Enzymatic Synthesis of 1-β-<i>O</i>-Acyl Glucuronides:  Highly Chemoselective Enzymatic Removal of Protecting Groups from Corresponding Methyl Acetyl Derivatives
  作者：Akiko Baba、Tadao Yoshioka

  DOI：10.1021/jo701547b

  日期：2007.12.1

  developed from the corresponding methyl acetyl derivatives 3a−f, which were stereospecifically synthesized from cesium salts of carboxylic acids 1a−f and methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-α-d-glucopyranuronate (2). Chemoselectivity of lipase AS Amano (LAS) in the hydrolytic removal of O-acetyl groups of 3a−f to provide methyl esters 4a−f was influenced by the nature of their 1-β-O-acyl groups; high

  的一系列的合成一种改进的和广泛适用的化学-酶促方法1-β- ö酰基葡糖苷酸5A - ˚F已从乙酰基衍生物相应的甲基开发3A - ˚F，将其立体专一从羧酸铯盐合成1a - f和2,3,4-三-O-乙酰基-1-溴-1-脱氧-α- d-吡喃葡萄糖醛酸甲酯（2）。在水解去除的脂肪酶AS天野（LAS）的化学选择性Ö的乙酰基团3A - ˚F提供甲酯4A -f受其1-β- O-酰基基团性质的影响；只有3b和3f才有很高的选择性。新近筛选出可替代LAS的罗氏链霉菌（CSR）的羧基酯酶显示出比LAS更高的对O-乙酰基的化学选择性。仅通过CSR化学选择性水解3a，3d和3e。CSR与LAS的组合比单独使用CSR产生的3c和3f水解效果更好。最终脱保护4a - f的甲基酯基团以提供图5a - ˚F是化学选择性通过使用脂肪酶从实现念珠菌南极类型B（CAL-B），以及来自猪肝脏（PLE）的酯酶，虽然CAL-B具有更
• Solvent-Dependent Mechanism and Stereochemistry of Mitsunobu Glycosylation with Unprotected Pyranoses
  作者：Hironori Takeuchi、Yusuke Fujimori、Yoshihiro Ueda、Hiromitsu Shibayama、Masaru Nagaishi、Tomoyuki Yoshimura、Takahiro Sasamori、Norihiro Tokitoh、Takumi Furuta、Takeo Kawabata

  DOI：10.1021/acs.orglett.0c01549

  日期：2020.6.19

  acidic glycosyl acceptors such as carboxylic acids, phenols, and imides, retaining its high stereoselectivity (33 examples). Glycosylation of a carboxylic acid with unprotected α-d-mannose proceeded also in an SN2 manner to directly afford a usually less accessible 1,2-cis-mannoside. One- or two-step total syntheses of five simple natural glycosides were performed using the glycosylation strategy presented

  在Mitsunobu条件下，在二恶烷中，用未保护的α- d-葡萄糖对苯甲酸高度立体选择性糖基化提出了一种S N 2机制，而在DMF中，对于非立体选择性糖基化则提出了一种S N 1机制。S N 2型立体选择性Mitsunobu糖基化通常可作为糖基供体与多种酸性糖基受体（如羧酸，酚和酰亚胺）结合使用，作为糖基供体，适用于各种未保护的吡喃糖，保持其高立体选择性（33个例子）。羧酸与未保护的α- d-甘露糖的糖基化也以S N 2方式进行，以直接提供通常较难获得的1,2-顺式-甘露糖苷。使用未保护的α- d-葡萄糖，使用此处介绍的糖基化策略进行五个简单天然糖苷的一步或两步总合成。
• Base‐Promoted Glycosylation Allows Protecting Group‐Free and Stereoselective <i>O</i>‐Glycosylation of Carboxylic Acids**
  作者：Hao Zuo、Chen Zhang、Yang Zhang、Dawen Niu

  DOI：10.1002/anie.202309887

  日期：2023.10.16

  Here we report a simple and general method to achieve fully unprotected, stereoselective glycosylation of carboxylic acids, employing bench‐stable allyl glycosyl sulfones as donors. Running the glycosylation reaction under basic conditions was crucial for the efficiencies and selectivities. Both the donor activation stage and the glycosidic bond forming stage of the process are compatible with free hydroxyl groups, thereby allowing for the use of fully unprotected glycosyl donors. This transformation is stereoconvergent, occurs under mild and metal‐free conditions at ambient temperature with visible light (455 nm) irradiation, and displays remarkable scope with respect to both reaction partners. Many natural products and commercial drugs, including an acid derived from the complex anticancer agent taxol, were efficiently glycosylated. Experimental studies provide insights into the origin of the stereochemical outcome.

  摘要我们在此报告了一种简单而通用的方法，该方法采用台式稳定的烯丙基糖基砜作为给体，实现了羧酸的完全无保护、立体选择性糖基化。在碱性条件下进行糖基化反应对效率和选择性至关重要。该过程的供体活化阶段和糖苷键形成阶段都与游离羟基兼容，因此可以使用完全无保护的糖基供体。这种转化具有立体转换性，在环境温度和可见光（455 纳米）照射下，在温和、无金属的条件下进行，而且对两个反应伙伴都有显著的影响。许多天然产物和商业药物，包括从复合抗癌剂紫杉醇中提取的一种酸，都被有效地糖基化了。实验研究为了解立体化学结果的起源提供了见解。