2,3,4-tri-O-benzyl-α-L-fucopyanosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 71672-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-α-L-fucopyanosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: (1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-8-[[(2R,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxymethyl]-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 71672-13-4
• 化学式: C₃₉H₄₈O₁₀
• 分子量: 676.804
• InChiKey: GLZLMYJDVOALEP-PPEAMGFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-6-脱氧-alpha-L-溴代半乳糖 在 sodium methylate 、 sodium hydride 、 potassium carbonate 、 碘甲烷 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 61.5h， 生成 2,3,4-tri-O-benzyl-α-L-fucopyanosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Stereoselective synthesis of α-O-fucosylated serine, threonine, tyrosine and saccharides

  摘要：

  在碘甲烷活化程序下，Boc-Ser/Thr/Tyr-OMe 2至4与2-吡啶基三-O-苄基-1-硫-β-L-岩藻糖供体1b偶联，以及几种糖醇5至7与该供体偶联，分别形成了α-连接的岩藻糖基化氨基酸甲酯结构单元8至10和α-连接的岩藻糖基糖11至13。

  DOI：

  10.1039/a704310d

文献信息

• A mild general method for the synthesis of ∝-linked disaccharides
  作者：G.Venugopal Reddy、Vinayak R. Kulkarni、Hari Babu Mereyala

  DOI：10.1016/s0040-4039(01)80711-5

  日期：1989.1

  Stereoselective ∝-glycosylations may be achieved using stable 2-pyridyl thioglycosides (anomeric mixture) having a non-participating 2-substituent as glycosyl donor and methyl iodide as an activator.

  使用具有非参与性2-取代基作为糖基供体和甲基碘作为活化剂的稳定的2-吡啶基硫代糖苷（端基异构体混合物）可以实现立体选择性的β-糖基化。
• Neighboring-Group Participation by C-2 Ether Functions in Glycosylations Directed by Nitrile Solvents
  作者：Chin-Sheng Chao、Ching-Yu Lin、Shaheen Mulani、Wei-Cheng Hung、Kwok-kong Tony Mong

  DOI：10.1002/chem.201100732

  日期：2011.10.17

  Ether‐protecting functions at C‐2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C‐2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2‐cis glycosyl

  当在腈溶剂混合物中进行反应时，已发现在C-2羟基处的醚保护功能在糖基化中起参与作用。参与机制基于C-2醚功能的氧原子的孤电子对和腈分子以顺式排列时的分子内相互作用。形成一个1,2-顺式糖基恶唑啉鎓中间体。这种参与，再加上糖基供体的异头作用，赋予糖基化较高的1,2-反式选择性。该概念的进一步应用导致了α-（1→5）-阿拉伯低聚物的高效制备。
• New Synthetic Methods and Reagents for Complex Carbohydrates. VII. Syntheses and Glycosylation Reactions of Glycopyranosyl Dimethylphosphinothioate Series Having a Nonparticipating Group at the C-2 Position
  作者：Takashi Yamanoi、Kazumi Nakamura、Shuji Sada、Masahiro Goto、Yoji Furusawa、Masaaki Takano、Ayumi Fujioka、Kenji Yanagihara、Yuzuru Satoh、Hideaki Hosokawa、Toshiyuki Inazu

  DOI：10.1246/bcsj.66.2617

  日期：1993.9

  nonparticipating group at the C-2 position could be easily prepared by reactions of the corresponding glycopyranose and dimethylphosphinothioyl chloride using butyllithium as a base in tetrahydrofuran. These dimethylphosphinothioates are stable at room temperature and gave the corresponding α-glycosides, predominantly in good yields, by reactions with alcohols using silver perchlorate as an activator in the

  在四氢呋喃中使用丁基锂作为碱，通过相应的吡喃糖和二甲基硫代膦酰氯反应，可以很容易地制备在 C-2 位具有非参与基团的几种吡喃糖基二甲基硫代膦酸酯。这些二甲基硫代膦酸酯在室温下是稳定的，并且在室温下在苯中的分子序列 4A 存在下，通过使用高氯酸银作为活化剂与醇反应，得到相应的 α-糖苷，主要是产率良好。此外，联合使用碘和催化量的高氯酸三苯甲酯作为一种新的活化系统而不是高氯酸银，对于这种糖苷化是有效的。此外，使用本方法制备了H-二糖和Lewis X抗原的合成中间体。
• A novel O -fucosylation strategy preactivated by ( p -Tol) 2 SO/Tf 2 O and its application for the synthesis of Lewis blood group antigen Lewis a
  作者：Cui-yun Li、Guang-jian Liu、Wei Du、Yuan Zhang、Guo-wen Xing

  DOI：10.1016/j.tetlet.2017.04.056

  日期：2017.5

  Based on a preactivation strategy using (p-To1)(SO)-S-2/Tf2O, a new O-fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent alpha-stereoselectivities of the fucosylation were obtained with secondary sugar alcohol as acceptors. Moreover, the novel fucosylation strategy was successfully applied to the synthesis of an important Lewis blood group antigen Lewis(a), which was obtained in nine linear steps with 27% overall yield. (C) 2017 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of α-O-fucosylated serine, threonine, tyrosine and saccharides
  作者：Hari Babu Mereyala、Srinivas Reddy Gurrala、Rajendrakumar Reddy Gadikota

  DOI：10.1039/a704310d

  日期：——

  Stereoselective fucosylation of Boc-Ser/Thr/Tyr-OMe 2–4 and several saccharide alcohols 5–7 by coupling with 2-pyridyl tri-O-benzyl-1-thio-β-L-fucosyl donor 1b under iodomethane activation procedure results in the formation of α-linked fucosylated amino acid methyl ester building blocks 8–10 and α-linked fucosyl saccharides 11–13, respectively.

  在碘甲烷活化程序下，Boc-Ser/Thr/Tyr-OMe 2至4与2-吡啶基三-O-苄基-1-硫-β-L-岩藻糖供体1b偶联，以及几种糖醇5至7与该供体偶联，分别形成了α-连接的岩藻糖基化氨基酸甲酯结构单元8至10和α-连接的岩藻糖基糖11至13。