cholesteryl 2,3,4,6-tetra-O-benzoyl β-D-galactopyranoside | 143520-25-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholesteryl 2,3,4,6-tetra-O-benzoyl β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl benzoate
• CAS: 143520-25-6
• 化学式: C₆₁H₇₂O₁₀
• 分子量: 965.237
• InChiKey: KSVPGSJKVQUDCL-QVYYRJIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.3
• 重原子数：
  71
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  cholesteryl 2,3,4,6-tetra-O-benzoyl β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 以75%的产率得到cholesteryl β-D-galactopyranoside
  参考文献：
  名称：

  Sugar/Steroid/Sugar Conjugates:  Sensitivity of Lipid Binding to Sugar Structure

  摘要：

  [GRAPHIC]Three steroids, each bearing a sugar on rings A and D, have been synthesized. Their effect on the "melting" behavior of a lipid bilayer depends on whether the sugar is glucose, galactose, or mannose. Packing constraints dictate how the lipid bilayer responds to the sugars.

  DOI：

  10.1021/ol030084r
• 作为产物：
  描述：

  2,3,4,6-四-O-苯甲酰基-D-吡喃半乳糖苷 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 cholesteryl 2,3,4,6-tetra-O-benzoyl β-D-galactopyranoside
  参考文献：
  名称：

  Sugar/Steroid/Sugar Conjugates:  Sensitivity of Lipid Binding to Sugar Structure

  摘要：

  [GRAPHIC]Three steroids, each bearing a sugar on rings A and D, have been synthesized. Their effect on the "melting" behavior of a lipid bilayer depends on whether the sugar is glucose, galactose, or mannose. Packing constraints dictate how the lipid bilayer responds to the sugars.

  DOI：

  10.1021/ol030084r

文献信息

• An efficient construction of 1,2-trans-β-glycosidic linkages capitalizing on glycopyranosyl N,N,N′,N′-tetramethylphosphroamidates as shelf-stable glycosyl donors
  作者：Shun-ichi Hashimoto、Yuki Yanagiya、Takeshi Honda、Hideki Harada、Shiro Ikegami

  DOI：10.1016/s0040-4039(00)92679-0

  日期：1992.6

  stereocontrolled 1,2-trans-β-glycosidation reaction with or without neighbouring group participation has been developed by using benzyl- or benzoyl-protected glycopyranosyl N,N,N',N'-tetramethylphosphoroamidates as shelf-stable glycosyl donors in the presence of trimethylsilyl trifluoromethanesulfonate or boron trifluoride etherate. Several notable features of the present method not observed with the diphenyl

  通过使用苄基或苯甲酰基保护的吡喃葡萄糖基N，N，N'，N'-四甲基磷酰胺基酸酯作为在货架上稳定的糖基供体，已经开发了具有或不具有邻近基团参与的高度立体控制的1,2-反式-β-糖苷化反应。存在三甲基甲硅烷基三氟甲磺酸盐或三氟化硼醚化物。还描述了用磷酸二苯酯法未观察到的本方法的几个显着特征。
• <i>O</i>-Glycosylation Enabled by <i>N-</i>(Glycosyloxy)acetamides
  作者：Miao Liu、Bo-Han Li、De-Cai Xiong、Xin-Shan Ye

  DOI：10.1021/acs.joc.8b01003

  日期：2018.8.3

  A novel glycosylation protocol has been established by using N-(glycosyloxy)acetamides as glycosyl donors. The N-oxyacetamide leaving group in donors could be rapidly activated in the presence of Cu(OTf)2 or SnCl4 under microwave irradiation. This glycosylation process afforded the coupled products in high yields, and the reaction enjoyed a broad substrate scope, even for disarmed donors and hindered

  通过使用N-（糖基氧基）乙酰胺作为糖基供体已经建立了新的糖基化方案。在微波辐射下，存在Cu（OTf）2或SnCl 4的情况下，供体中的N-氧乙酰胺离去基团可以快速活化。该糖基化过程以高收率提供了偶联产物，并且该反应享有广泛的底物范围，即使对于缴械的供体和受阻的受体也是如此。供体的容易获得，N-（糖基氧基）乙酰胺的高稳定性以及小的离去基团使该方法非常实用。
• An Anomeric <scp>Base‐Tolerant</scp> Ester of <scp>8‐Alkynyl</scp> ‐1‐naphthoate for Gold(I)‐Catalyzed Glycosylation Reaction
  作者：Xiaojuan Zhang、Peng Xu、Zhengbing Zhou、Yazhou Zhang、Biao Yu、Yugen Zhu

  DOI：10.1002/cjoc.202300005

  日期：——

  samples, which mainly relies on the key glycosylation reaction. Consistent with enormous efforts to develop leaving groups for establishing robust glycosylation protocols, we herein disclose a structurally novel leaving group of 8-phenylethynyl-1-naphthoate that is able to enable efficient glycosylation reactions under the extremely mild condition of gold(I)-catalysis. Notably, the anomeric naphthoate possesses

  鉴于碳水化合物的极端复杂性和多样性，对均质寡糖的有效方法仍然有限。化学合成是获取均质样品最可靠的方法之一，主要依赖于关键的糖基化反应。与开发离去基团以建立稳健的糖基化方案的巨大努力一致，我们在此公开了一种结构新颖的 8-phenylethynyl-1-naphthoate 离去基团，它能够在金 (I) 催化的极其温和的条件下实现有效的糖基化反应. 值得注意的是，异头萘甲酸酯具有前所未有的碱稳定性，与碳水化合物异头位置的常规酯基形成鲜明对比，这赋予了它与多种化学转化的高度相容性。此外，本发明以 8-苯基乙炔基-1-萘甲酸酯作为离去基团的糖基化方案能够实现最低限度保护的糖基化过程。机理研究揭示了 8-phenylethynyl-1-naphthoate 的独特结构，这是造成这些特性的原因。
• Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides
  作者：Gopalsamy Sureshkumar、Srinivas Hotha

  DOI：10.1016/j.tetlet.2007.07.015

  日期：2007.9

  Propargyl 1,2-orthoesters are identified as glycosyl donors. Various glycosides and disaccharides were synthesized in a stereoselective manner using AuBr3 as the promoter. AuBr3 may activate the alkyne resulting in the formation of a 1,2-dioxolenium ion and also behaves as a Lewis acid to facilitate the attack of the glycosyl acceptor. The versatility of the protocol was demonstrated using a panel of aglycones comprising aliphatic, alicyclic, steroidal and sugar alcohols. (C) 2007 Elsevier Ltd. All rights reserved.
• Glycosylation of alcohols using glycosyl boranophosphates as glycosyl donors
  作者：Shiro Tatsumi、Fumiko Matsumura、Natsuhisa Oka、Takeshi Wada

  DOI：10.1016/j.tetlet.2013.04.032

  日期：2013.7

  A novel glycosylation that uses glycosyl boranophosphate triesters as glycosyl donors and trityl cation (Tr+) as an activator was developed. Two types of reactions were studied: (1) the boranophosphate triester was activated with TrNTf2 to react with an alcohol and (2) O-trityl ethers worked as both glycosyl acceptors and Tr+ sources. The latter gave better results and the desired O-glycosylation products were rapidly generated and isolated in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.