allyl 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside | 1095377-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside
• 英文别名: allyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside；1-O-allyl-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside；(2R,3S,4R,6R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxane
• CAS: 1095377-23-3
• 化学式: C₃₀H₃₄O₅
• 分子量: 474.597
• InChiKey: FCDXCSGVVOLLNB-CSBHBGLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 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 、 3-溴丙烯 在 sodium hydride 作用下， 以 1,4-二氧六环 、 mineral oil 为溶剂， 反应 5.17h， 以70%的产率得到allyl 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside
  参考文献：
  名称：

  使用异头 O-烷基化/芳基化立体选择性合成 2-脱氧-β-糖苷

  摘要：

  异头 O-烷基化/芳基化应用于 2-脱氧-β-糖苷的合成。在二恶烷中用 NaH 处理乳糖醇，然后加入亲电子试剂，以高产率和高选择性形成 2-脱氧-β-糖苷。这里观察到的高β-选择性证明了在动力学控制下立体选择性形成缩醛的强大立体电子效应。

  DOI：

  10.1021/ol8022006

文献信息

• TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
  作者：Mei-Yuan Hsu、Yi-Pei Liu、Sarah Lam、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3762/bjoc.12.164

  日期：——

  The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.

  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。
• 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。
• Aluminium triflate catalysed O-glycosidation: temperature-switched selective Ferrier rearrangement or direct addition with alcohols
  作者：D. Bradley G. Williams、Sandile B. Simelane、Henok H. Kinfe

  DOI：10.1039/c2ob25540e

  日期：——

  A temperature-controlled mechanism switch between the Al(OTf)3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the stereochemistry and nature of the protecting groups on the glycal substrate.

  提出了在Al（OTf）3催化的醇直接添加或某些糖基中的Ferrier重排反应之间的温度控制机制切换。研究了范围和局限性以及糖基上保护基的立体化学和性质的影响。
• AuCl₃-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives
  作者：Robin Jeanneret、Carlo Walz、Maarten van Meerbeek、Sarah Coppock、M. Carmen Galan

  DOI：10.1021/acs.orglett.2c02530

  日期：2022.9.2

  A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α′-linked 2-deoxy trehalose analogues via AuCl3-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Brønsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals.

  描述了一种使用半缩醛糖基供体和受体通过 AuCl 3催化的脱水糖基化直接获得 1,1-α,α'-连接的 2-脱氧海藻糖类似物的实用、催化和高度立体选择性的新方法。该方法依赖于在其他反应性较低的半缩醛存在下，三苯甲基化 2-脱氧半缩醛的化学选择性布朗斯台德酸型活化。
• Stereoselective Synthesis of 2-Deoxy-β-glycosides Using Anomeric O-Alkylation/Arylation
  作者：William J. Morris、Matthew D. Shair

  DOI：10.1021/ol8022006

  日期：2009.1.1

  Anomeric O-alkylation/arylation is applied to the synthesis of 2-deoxy-β-glycosides. Treatment of lactols with NaH in dioxane followed by the addition of electrophiles leads to the formation of 2-deoxy-β-glycosides in high yield and high selectivity. The high β-selectivity observed here demonstrates a powerful stereoelectronic effect for the stereoselective formation of acetals under kinetic control

  异头 O-烷基化/芳基化应用于 2-脱氧-β-糖苷的合成。在二恶烷中用 NaH 处理乳糖醇，然后加入亲电子试剂，以高产率和高选择性形成 2-脱氧-β-糖苷。这里观察到的高β-选择性证明了在动力学控制下立体选择性形成缩醛的强大立体电子效应。