cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranoside
• 英文别名: (2R,3R,4R,6S)-6-cyclohexyloxy-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane
• 化学式: C₃₃H₄₀O₅
• 分子量: 516.678
• InChiKey: OWDDAYROLXCALF-NXVJRICRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 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-tri-O-benzyl-2-deoxy-α/β-D-galactopyranosyl phenylpropiolate 、 环己醇 在 gold(III) chloride 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  无添加剂的金（III）催化使用苯丙丙酸酯糖苷作为供体的2-脱氧糖苷的立体选择性合成。

  摘要：

  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。

  DOI：

  10.1002/asia.201900888

文献信息

• 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。
• Different reaction routes found in acid-catalyzed glycosylation of endo- and exo-glycals: competition between Ferrier rearrangement and protonation
  作者：Hui-Chang Lin、Wen-Ping Du、Chih-Chun Chang、Chun-Hung Lin

  DOI：10.1016/j.tetlet.2005.05.061

  日期：2005.7

  products is often obtained resulting from Ferrier rearrangement and protonation. The former reaction exclusively takes place with the t-butyl carbonate or hydroxyl substituent at the C3 position of endo-glycals, while the latter mainly occurs in the glycosylation of exo-glycals with allyl benzyl ether or acetate. In addition to the substituent effect, protecting groups are critical to determine the

  内-和外-糖的酸介导的糖基化已经以良好或优异的产率进行，其中经常由于费里耳重排和质子化而获得两种产物的混合物。前者反应只发生与吨丁基碳酸酯或在C3位羟基取代基内切-glycals，而后者主要发生在糖基化外型-glycals与烯丙基苄基醚或乙酸盐。除取代基作用外，保护基对于确定活性和有利的反应途径也至关重要。此外，该方法适用于O-，C-和N-亲核试剂。
• Dehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester
  作者：Sanjay Manhas、Mark S. Taylor

  DOI：10.1016/j.carres.2018.10.002

  日期：2018.12

  An N-methylpyridinium-4-boronic ester acts as a catalyst for dehydrative glycosidations of 2-deoxy sugar-derived hemiacetals. The catalytic protocol is tolerant of functionalized acceptors, including alcohols bearing isopropylidene ketal, tert-butyl carbamate or benzyl carbamate groups. The results demonstrate that organoboron- catalyzed substitution reactions of alcohols, which have previously been conducted on p-activated (benzylic, allylic or propargylic) substrates, can also be used to achieve C-O bond formation from carbohydratederived hemiacetals.
• Stereoselective glycosylation of endo-glycals by microwave- and AlCl3-assisted catalysis
  作者：Hui-Chang Lin、Jia-Fu Pan、Yen-Bo Chen、Zi-Ping Lin、Chun-Hung Lin

  DOI：10.1016/j.tet.2011.05.124

  日期：2011.8

  alpha-2-Deoxyglycosides were synthesized in good to excellent yields by microwave-assisted reaction of endo-glycals with various O-nucleophiles in the presence of catalytic amount of AlCl3. These glycosyl additions occurred with high alpha-stereoselectivity and were complete in 5-35 min in 65-93% yield. (C) 2011 Elsevier Ltd. All rights reserved.
• 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。