isopropyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranoside | 380450-53-3

• 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-α-D-galactopyranoside
• 英文别名: (2R,3R,4R,6S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-propan-2-yloxyoxane
• CAS: 380450-53-3
• 化学式: C₃₀H₃₆O₅
• 分子量: 476.613
• InChiKey: JGOHAMQPLGGOLX-GKIKGMKOSA-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：

  3,4,6-三邻苄基半乳醛 、 异丙醇 在 三甲基硅咪唑 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到isopropyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  The synthesis of 2-deoxy-α-d-glycosides from d-glycals catalyzed by TMSI and PPh3

  摘要：

  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.

  DOI：

  10.1016/j.carres.2012.06.004

文献信息

• Fluorine-Directed β-Galactosylation: Chemical Glycosylation Development by Molecular Editing
  作者：Estelle Durantie、Christoph Bucher、Ryan Gilmour

  DOI：10.1002/chem.201200468

  日期：2012.6.25

  Validation of the 2‐fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2‐fluoro‐3,4,6‐tri‐O‐benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization

  提出了将2-氟取代基作为控制化学糖基化反应的惰性指导基团的验证方法。一项分子编辑研究表明，通过使用2-氟-3,4,6-三-O-苄基吡喃葡萄糖基三氯乙酰亚氨酸酯（TCA）支架，糖基化过程中非对映异构控制的异常水平是2 R，3 S，4的结果S立体三合会。这项研究还表明，C4的差向异构作用会导致β选择性大大提高（高达β/α300：1）。
• 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。
• 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.