isopropyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranoside
• 英文别名: 1-O-isopropyl-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranose；isoproropyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside；isopropyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside；isopropyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside；1-O-isopropyl-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose；isopropyl 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside；(2R,3S,4R,6R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-propan-2-yloxyoxane
• 化学式: C₃₀H₃₆O₅
• 分子量: 476.613
• InChiKey: JGOHAMQPLGGOLX-CSBHBGLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranose 在 吡啶 、 氢氟酸 、 硫酸酯 、 zirconium(IV) oxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 isopropyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Novel Stereocontrolled Glycosidations of 2-Deoxyglucopyranosyl Fluoride Using a Heterogeneous Solid Acid, Sulfated Zirconia (SO₄/ZrO₂)

  摘要：

  开发了一种新型立体选择性的2-脱氧-α-D-葡萄糖苷氟化物的糖苷化反应，采用了一种均匀且环保的固体酸——硫酸锆（SO4/ZrO2）。在25°C下，使用SO4/ZrO2在CH3CN中反应1小时，能够主要得到相应的2-脱氧-α-D-葡萄糖苷。而在0°C下，使用SO4/ZrO2与分子筛5A在乙醚中反应1小时，则能选择性地获得相应的2-脱氧-β-D-葡萄糖苷。

  DOI：

  10.1055/s-1999-2742

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。
• Additive‐Free Gold(III)‐Catalyzed Stereoselective Synthesis of 2‐Deoxyglycosides Using Phenylpropiolate Glycosides as Donors
  作者：Mukta Shaw、Amit Kumar

  DOI：10.1002/asia.201900888

  日期：2019.12.13

  Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields

  在无外部添加剂的条件下，使用金（III）盐作为催化剂，可从台式稳定且易于合成的脱氧苯丙酸丙二醇酯（D-PPGs）中实现脱氧糖苷的立体选择性合成。在简单的催化系统下，D-PPG与多种糖和非糖受体反应，以高至优异的收率产生主要的α-立体选择性O / N-脱氧糖苷，并再生易于分离和重用的苯丙酸。在优化的反应条件下，含有武装和解除武装团体的脱氧PPG能够很好地存活。另外，展示了D-PPG的正交性质，并且还合成了1，1'-连接的海藻糖型糖。
• 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。
• Direct Dehydrative Glycosylation Catalyzed by Diphenylammonium Triflate
  作者：Mei-Yuan Hsu、Sarah Lam、Chia-Hui Wu、Mei-Huei Lin、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3390/molecules25051103

  日期：——

  dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

  描述了在微波辐射下由三氟甲磺酸二苯基铵催化的碳水化合物半缩醛的直接脱水糖基化的方法。武装和解除武装的糖基-C1-半缩醛供体均以中等至优异的产率有效糖基化，无需任何干燥剂和化学计量添加剂。该方法已成功应用于固相糖基化。