methyl 4,6-O-cyclohexylidene-2,3-di-O-(benzyl-d7)-1-thio-β-D-glucopyranoside | 854735-94-7

• 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-2,3-di-O-(benzyl-d7)-1-thio-β-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8S,8aR)-7,8-bis[dideuterio-(2,3,4,5,6-pentadeuteriophenyl)methoxy]-6-methylsulfanylspiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]
• CAS: 854735-94-7
• 化学式: C₂₇H₃₄O₅S
• 分子量: 484.519
• InChiKey: DZUNRXOOTDJSAC-ULEHRKPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-cyclohexylidene-2,3-di-O-(benzyl-d7)-1-thio-β-D-glucopyranoside 、 4-methoxyphenyl 2-O-benzyl-d7-4,6-O-cyclohexylidene-α-D-mannopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲烷磺酸甲酯 作用下， 反应 24.0h， 生成 4-methoxyphenyl 4,6-O-cyclohexylidene-2,3-di-O-(benzyl-d7)-α-D-glucopyranosyl-(1->3)-2-O-(benzyl-d7)-4,6-O-cyclohexylidene-α-D-mannopyranoside
  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：

  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

文献信息

• High throughput screening of O-glycosylation conditions
  作者：Akihiro Ishiwata、Yukishige Ito

  DOI：10.1016/j.tetlet.2005.03.066

  日期：2005.5

  We report a novel methodology for rapid and quantitative screening of O-glycosylation reactions of application to the analysis of parallel reaction systems. Our system exploits perdeuterated benzyl (Bn-d(7)) ether, and stereoselectivity and yield are evaluated by H-1 NMR and MALDI-TOF MS, respectively. This paper summarizes over 240 screenings of 1 -> 3 linkage formation between glucose residues targeting the alpha-isomer in high yield. (c) 2005 Elsevier Ltd. All rights reserved.