6-O-(2,3,4-tri-O-benzyl-L-rhamnopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 126330-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(2,3,4-tri-O-benzyl-L-rhamnopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• CAS: 126330-71-0
• 化学式: C₃₉H₄₈O₁₀
• 分子量: 676.804
• InChiKey: GLZLMYJDVOALEP-PGRKOHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 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：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  3,4-di-O-acetyl-1,2-O-methoxyethylidene-β-L-rhamnopyranose 在 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 、 mercury dibromide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 paraffin 为溶剂， 反应 9.0h， 生成 6-O-(2,3,4-tri-O-benzyl-L-rhamnopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis and glycosylation of pyrimidin-2-yl 1-thio-α-d-manno- and -α-l-rhamnopyranoside

  摘要：

  Pyrimidin-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-alpha-D-mannopyrano side (9), pyrimidin-2-yl 2,3,4-tri-O-benzyl-alpha-L-rhamnopyranoside (10), pyrimidin-2-yl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-alpha-D-mannopyranoside (7), and pyrimidin-2-y1 2-O-acetyl-3,4-di-O-benzyl-1-thio-alpha-L-rhamnopyranoside (8) were prepared almost quantitatively fi om the corresponding protected 1,2-O-methoxyethylidene-beta-D-manno-or-beta-L-rhamnopyranose with 2-mercaptopyrimidine in the presence of mercuric bromide. Coupling reactions of the thioglycosides promoted by silver triflate with suitable glycosyl accepters afforded 1,2-trans linked disaccharides. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00164-5

文献信息

• Stereoselective synthesis of α-linked saccharides by use of per O-benzylated 2-pyridyl 1-thio hexopyranosides as glycosyl donors and methyl iodide as an activator
  作者：Hari Babu Mereyala、G Venugopal Reddy

  DOI：10.1016/s0040-4020(01)86571-6

  日期：1991.8

  D-manno-(3) and L-rhamno-(4) configurations have been efficiently coupled with diverse sugar alcohols (6,8–11) on activation by methyl iodide to obtain the α-linked disaccharides (7,12–19). Coupling of donor 1 with the disaccharide acceptor 20 and the disaccharide donor 5 with 8 to obtain α-linked trisaccharides 21 and 22 is also described. A possible mechanism for the α-selectivity is also discussed

  描述了一种新的，实用的，立体选择性糖苷化方法，其中每个D-葡萄糖-（1），D-半乳糖-（2），D-甘露聚糖-（- ）的O-苄基化2-吡啶基1-硫代-α/β-己吡喃糖基3）和L-鼠李糖（4）构型已通过甲基碘活化与各种糖醇（6,8-11）有效偶联，获得了α-连接的二糖（7,12-19）。供体1与二糖受体20的偶联，以及二糖供体5与8的偶联，以获得α-连接的三糖21和22也进行了描述。还讨论了α选择性的可能机理。
• Stereoselective synthesis of β-rhamnopyranosides via gold(<scp>i</scp>)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors
  作者：Yugen Zhu、Zhengnan Shen、Wei Li、Biao Yu

  DOI：10.1039/c5ob02551f

  日期：——

  An effective β-rhamnosylation protocol has been developed by using α-rhamnopyranosyl ortho-hexynyl-para-nitro-benzoates as donors and Ph₃PAuBArF4 as a catalyst.

  已开发出一种有效的β-葡萄糖苷化协议，该协议使用α-葡萄糖苷基-邻-己炔基-对-硝基苯甲酸酯作为供体，Ph3PAuBArF4作为催化剂。
• 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。
• Visible-light-induced photoacid catalysis: application in glycosylation with <i>O</i>-glycosyl trichloroacetimidates
  作者：Gaoyuan Zhao、Juncheng Li、Ting Wang

  DOI：10.1039/d1cc04887b

  日期：——

  The development of visible-light-induced photoacid catalyzed glycosylation is reported.

  可见光诱导的光酸催化糖基化反应的发展被报道。
• New Synthetic Methods and Reagents for Complex Carbohydrates. VIII. Stereoselective<i>α</i>- and<i>β</i>-Mannopyranoside Formation from Glycosyl Dimethylphosphinothioates with the C-2 Axial Benzyloxyl Group
  作者：Takashi Yamanoi、Kazumi Nakamura、Hiroshi Takeyama、Kenji Yanagihara、Toshiyuki Inazu

  DOI：10.1246/bcsj.67.1359

  日期：1994.5

  The reactions of mannopyranosyl dimethylphosphinothioates and alcohols using silver perchlorate as an activator in the presence of molecular sieves 4A in benzene at room temperature gave the 1,2-trans-α-mannopyranosides in good yields. On the other hand, 1,2-cis-β-mannopyranosides could be obtained from the dimethylphosphinothioates by the combined use of iodine and 5 mol% triphenylmethyl perchlorate

  吡喃甘露糖基二甲基硫代膦酸酯和醇使用高氯酸银作为活化剂，在分子筛 4A 存在下，在室温下在苯中反应，以良好的收率得到 1,2-反式-α-吡喃甘露糖苷。另一方面，通过结合使用碘和 5 mol% 高氯酸三苯甲酯作为活化系统，可以从二甲基硫代膦酸酯中获得 1,2-顺式-β-吡喃甘露糖苷。描述了通过这些方法合成糖蛋白的 αMan(1→6)[αMan(1→3)]Man 和 βMan(1→4)GlcNAc 单元的衍生物。