cholesteryl (3,4,6-tri-O-benzyl-2-deox-β-D-glucopyranoside)

• 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 (3,4,6-tri-O-benzyl-2-deox-β-D-glucopyranoside)
• 英文别名: Cholesteryl 2,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside；cholesteryl-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside；cholesteryl-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside；(2R,3S,4R,6R)-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]-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane
• 化学式: C₅₄H₇₄O₅
• 分子量: 803.179
• InChiKey: DDDUMAVYAFHRRT-NEBBVFTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  59
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,6-三-氧-苄基-2-脱氧-D-吡喃葡萄糖 在 4 A molecular sieve 、 lithium perchlorate 、 sodium hydride 、 cesium fluoride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 cholesteryl (3,4,6-tri-O-benzyl-2-deox-β-D-glucopyranoside)
  参考文献：
  名称：

  Schene, Heidrun; Waldmann, Herbert, Chemical Communications, 1998, # 24, p. 2759 - 2760

  摘要：

  DOI：

文献信息

• An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation
  作者：An-Hsiang Adam Chu、Andrei Minciunescu、Vittorio Montanari、Krishna Kumar、Clay S. Bennett

  DOI：10.1021/ol5004059

  日期：2014.3.21

  iodonium salt phenyl(trifluoroethyl)iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68–97% yield. The reaction conditions are mild and do not require strict exclusion of air and moisture. The operational simplicity of the method should allow experimentalists with a limited synthetic background

  空气和水稳定的碘鎓盐苯基（三氟乙基）碘鎓三氟甲磺酰亚胺在室温下可激活硫代糖苷以进行糖基化。武装和解除武装的硫糖苷都以 68-97% 的产率迅速进行糖基化。反应条件温和，不需要严格排除空气和水分。该方法的操作简单性应该允许具有有限合成背景的实验者构建糖苷键。
• Glycosylation Reactions Using Phenyl(trifluoroethyl)iodonium Salts
  申请人：Trustees of Tufts College

  公开号：US20150099870A1

  公开（公告）日：2015-04-09

  Provided are methods for the preparation of glycosylation products, including those represented by formula I: Sugar-O—R′  I comprising the step of combining R′—OH, a glycosyl sulfide glycosyl donor (“thioglycoside donor”), a hypervalent iodine alkyl-transfer activating reagent, and a base. In an embodiment, the hypervalent iodine alkyl-transfer activating reagent is (phenyl(trifluoroethyl)iodonium triflimide).

  提供了制备糖基化产物的方法，包括由式I表示的那些： 糖-O—R′  I 包括将R′—OH、糖基硫醚糖基供体（“硫代糖苷供体”）、高价碘烷基转移活化试剂和碱结合的步骤。在一种实施例中，高价碘烷基转移活化试剂为（苯基(三氟乙基)碘三氟甲磺酰胺）。
• 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。
• Halide Effects on Cyclopropenium Cation Promoted Glycosylation with Deoxy Sugars: Highly α-Selective Glycosylations Using a 3,3-Dibromo-1,2-diphenylcyclopropene Promoter
  作者：Jason M. Nogueira、John Paul Issa、An-Hsiang Adam Chu、Jordan A. Sisel、Ryan S. Schum、Clay S. Bennett

  DOI：10.1002/ejoc.201200907

  日期：2012.9

  A mixture of 3,3-dibromocyclopropene and TBAI promotes highly α-selective glycosylation reactions (up to >20:1) by using deoxy sugar hemiacetal donors. The reaction provides a convenient method for generating highly reactive glycosyl donors in situ from shelf-stable starting materials. Both armed and disarmed sugars undergo the reaction, and selectivity is independent of the configuration of the donor

  3,3-二溴环丙烯和 TBAI 的混合物通过使用脱氧糖半缩醛供体促进高度 α 选择性糖基化反应（高达 >20:1）。该反应提供了一种方便的方法，用于从储存稳定的起始材料原位生成高反应性糖基供体。武装和解除武装的糖都会发生反应，选择性与供体糖的构型无关。
• Facile O-glycosylation of glycals using Glu-Fe₃O₄-SO₃H, a magnetic solid acid catalyst
  作者：Raju S. Thombal、Vrushali H. Jadhav

  DOI：10.1039/c6ra03305a

  日期：——

  A new glucose derived magnetic solid acid catalyst (Glu-Fe3O4-SO3H) was synthesized in a convenient and ecofriendly manner and well characterized using FTIR, PXRD, EDAX, SEM, and XPS which showed the presence of Fe3O4 embedded on the surface of the catalyst along with –SO3H, –OH and –COOH functional groups. This new heterogeneous catalyst was studied for synthesis of 2-deoxy galactosides/glucosides

  以方便，环保的方式合成了一种新型的葡萄糖衍生磁性固体酸催化剂（Glu-Fe 3 O 4 -SO 3 H），并通过FTIR，PXRD，EDAX，SEM和XPS对其进行了很好的表征，表明存在Fe 3 O 4与–SO 3 H，–OH和–COOH官能团一起嵌入催化剂表面。研究了这种新型多相催化剂，用于合成2-脱氧半乳糖苷/葡糖苷，具有良好的收率和选择性。而且，催化剂可以容易地用外磁力从反应中分离出来，并至少可重复使用四次，而每次循环后产物的产率没有任何明显的降低。