tert-butyl 3,4,6-tri-O-benzyl-α-D-arabino-hexopyranoside | 148625-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 3,4,6-tri-O-benzyl-α-D-arabino-hexopyranoside
• 英文别名: tert-butanyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside；tert-butyl 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside；1-O-t-butyl-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose
• CAS: 148625-56-3
• 化学式: C₃₁H₃₈O₅
• 分子量: 490.64
• InChiKey: UTNRVMSOMWNVQP-CSBHBGLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  溴甲苯 在 三甲基溴硅烷 、 sodium methylate 、 三苯基氧化膦 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 tert-butyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranoside 、 tert-butyl 3,4,6-tri-O-benzyl-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

  摘要：

  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。

  DOI：

  10.3762/bjoc.12.164

文献信息

• Organocatalytic Glycosylation by Using Electron-Deficient Pyridinium Salts
  作者：Somnath Das、Daniel Pekel、Jörg-M. Neudörfl、Albrecht Berkessel

  DOI：10.1002/anie.201503156

  日期：2015.10.12

  A new organocatalytic glycosylation method based on electron‐deficient pyridinium salts is reported. At ambient temperature and catalyst loadings as low as 1 mol %, 2‐deoxyglycosides were formed from benzyl‐ and silyl‐protected glycals and primary or secondary glycosyl acceptors, with excellent yields and anomeric selectivity. Mechanistic investigations point to alcohol–pyridinium conjugates (1,2‐addition

  报道了一种新的基于缺电子吡啶鎓盐的有机催化糖基化方法。在环境温度和低至1 mol％的催化剂负载量下，由苄基和甲硅烷基保护的糖基和伯或仲糖基受体形成2-脱氧糖苷，具有优异的收率和端基异构体选择性。机理研究表明，醇-吡啶共轭物（1,2-加成产物）是催化循环中的关键中间体。
• 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。
• The synthesis of 2-deoxy-α-d-glycosides from d-glycals catalyzed by TMSI and PPh3
  作者：Xi-Kai Cui、Ming Zhong、Xiang-Bao Meng、Zhong-Jun Li

  DOI：10.1016/j.carres.2012.06.004

  日期：2012.9

  2-Deoxyglycosides were synthesized in high alpha-selectivity by the direct addition of alcohols to D-glucal and D-galactal catalyzed by TMSI and PPh3. The acid labile isopropylidene group is tolerated under this condition. (C) 2012 Elsevier Ltd. All rights reserved.
• Glycosyl hydroperoxides derived from 2-deoxysugars
  作者：Barbara Szechner、Zofia Urbańczyk-Lipkowska、Marek Chmielewski

  DOI：10.1016/j.carres.2010.09.005

  日期：2010.11

  Oxidation of 3,4,6-tri-O-benzyl-2-deoxy-D-glucose and D-galactose or their t-butyl glycosides to the corresponding glycosyl hydroperoxides can be performed with hydrogen peroxide in the presence of an acid catalyst. Several reaction conditions and their influence on the effectiveness of the oxidation are discussed. Separation of the alpha - and beta-anomers of the glycosyl hydroperoxides was achieved through mixed peroxide formation by reaction of the hydroperoxide group with 2-methoxypropene and subsequent deprotection. (C) 2010 Elsevier Ltd. All rights reserved.