methyl 4,6-O-cyclohexylidene-1-thio-β-D-glucopyranoside | 854735-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-O-cyclohexylidene-1-thio-β-D-glucopyranoside
• CAS: 854735-98-1
• 化学式: C₁₃H₂₂O₅S
• 分子量: 290.381
• InChiKey: MZZHEWBDOQJYBC-OOCWMUITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-cyclohexylidene-1-thio-β-D-glucopyranoside 、 苄基溴-d7 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以70%的产率得到methyl 4,6-O-cyclohexylidene-2,3-di-O-(benzyl-d7)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synergistic solvent effect in 1,2-cis-glycoside formation

  摘要：

  Construction of three continuous 1,2-cis-alpha-glucosidic linkages was achieved in optimized solvent system. High-throughput optimization was conducted, by using substrates protected by perdeuterated benzyl (Bn-d(7)) groups. It enabled facile evaluation of yield and stereoselectivity with H-1 NMR and MALDI-TOF MS, respectively. We found that CHCl3 and ethereal solvent had a synergetic effect to enhance the a-selectivity. The optimized solvent systems in CHCl3/CPME and CHCl3/Et2O were applied to the linear synthesis of Glc alpha 1-2Glc alpha 1-3Glc alpha l-3Man (GlC(3)Man(1)), which was achieved in 86% overall stereo selectivity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.087
• 作为产物：
  描述：

  环己酮二甲缩酮 、 甲基-beta-D-硫代吡喃葡萄糖苷 在 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl 4,6-O-cyclohexylidene-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synergistic solvent effect in 1,2-cis-glycoside formation

  摘要：

  Construction of three continuous 1,2-cis-alpha-glucosidic linkages was achieved in optimized solvent system. High-throughput optimization was conducted, by using substrates protected by perdeuterated benzyl (Bn-d(7)) groups. It enabled facile evaluation of yield and stereoselectivity with H-1 NMR and MALDI-TOF MS, respectively. We found that CHCl3 and ethereal solvent had a synergetic effect to enhance the a-selectivity. The optimized solvent systems in CHCl3/CPME and CHCl3/Et2O were applied to the linear synthesis of Glc alpha 1-2Glc alpha 1-3Glc alpha l-3Man (GlC(3)Man(1)), which was achieved in 86% overall stereo selectivity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.087

文献信息

• NAP Ether Mediated Intramolecular Aglycon Delivery: A Unified Strategy for 1,2-<i>cis</i>-Glycosylation
  作者：Akihiro Ishiwata、Yuichi Munemura、Yukishige Ito

  DOI：10.1002/ejoc.200800249

  日期：2008.9

  of 1,2-cis-glycosides through naphthylmethyl (NAP) ether mediated intramolecular aglycon derivery (IAD) has been developed. Stereospecific constructions of various 1,2-cis linkages, as in β-mannopyrano-, β-arabinofurano-, and α-glucopyranosides, were achieved through NAP-IAD. This methodology was successfully applied to the synthesis of Glca(1→2)-Glcα(1→3)-Glcα(1→3)Man (Glc 3 Man 1 ), the nonreducing

  已经开发了一种通过萘甲基 (NAP) 醚介导的分子内苷元衍生 (IAD) 立体选择性构建 1,2-顺式糖苷的方法。通过 NAP-IAD 实现了各种 1,2-顺式连接的立体特异性构建，如β-吡喃甘露糖苷、β-阿拉伯呋喃糖苷和α-吡喃葡萄糖苷。该方法成功应用于合成十四糖Glc 3 Man 9 GlcNAc 2 的非还原末端结构Glca(1→2)-Glcα(1→3)-Glcα(1→3)Man (Glc 3 Man 1 ) ，所有 N 连接聚糖的常见前体。
• Synergistic solvent effect in 1,2-cis-glycoside formation
  作者：Akihiro Ishiwata、Yuichi Munemura、Yukishige Ito

  DOI：10.1016/j.tet.2007.10.087

  日期：2008.1

  Construction of three continuous 1,2-cis-alpha-glucosidic linkages was achieved in optimized solvent system. High-throughput optimization was conducted, by using substrates protected by perdeuterated benzyl (Bn-d(7)) groups. It enabled facile evaluation of yield and stereoselectivity with H-1 NMR and MALDI-TOF MS, respectively. We found that CHCl3 and ethereal solvent had a synergetic effect to enhance the a-selectivity. The optimized solvent systems in CHCl3/CPME and CHCl3/Et2O were applied to the linear synthesis of Glc alpha 1-2Glc alpha 1-3Glc alpha l-3Man (GlC(3)Man(1)), which was achieved in 86% overall stereo selectivity. (c) 2007 Elsevier Ltd. All rights reserved.