tert-butyl N-[4-[(2S,3R,4R,5S,6R)-3-azido-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-hydroxyoxan-2-yl]-1-hydroxy-2-(hydroxymethyl)but-3-yn-2-yl]carbamate | 364631-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[4-[(2S,3R,4R,5S,6R)-3-azido-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-hydroxyoxan-2-yl]-1-hydroxy-2-(hydroxymethyl)but-3-yn-2-yl]carbamate
• CAS: 364631-76-5
• 化学式: C₄₄H₇₂N₄O₉Si₃
• 分子量: 885.334
• InChiKey: SPVQVNNZWNAOOR-APNVPUNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.36
• 重原子数：
  60
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[4-[(2S,3R,4R,5S,6R)-3-azido-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-hydroxyoxan-2-yl]-1-hydroxy-2-(hydroxymethyl)but-3-yn-2-yl]carbamate 在 palladium on activated charcoal camphor-10-sulfonic acid 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 18.0h， 生成 tert-butyl N-[(2R,3S,4R,5R,6S,9S)-5-azido-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-9-(hydroxymethyl)-1,7-dioxaspiro[5.5]undec-10-en-9-yl]carbamate 、 tert-butyl N-[(2R,3S,4R,5R,6S,9R)-5-azido-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-9-(hydroxymethyl)-1,7-dioxaspiro[5.5]undec-10-en-9-yl]carbamate
  参考文献：
  名称：

  New design concepts for constraining glycosylated amino acids

  摘要：

  In an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, two constrained glycopeptides based on the alpha -N-acetylgalactosaminyl serine substructure were chosen for synthesis. These compounds representing one of the two possible gauche conformations of the D-serine and L-serine configurations of the parent substructure were successfully prepared in reasonable overall yield through a convergent strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00545-2
• 作为产物：
  描述：

  (5-甲酰基-2,2-二甲基-1,3-二氧六环-5-基)氨基甲酸叔丁酯 在 正丁基锂 、 camphor-10-sulfonic acid 、 水 、 甲基锂 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.58h， 生成 tert-butyl N-[4-[(2S,3R,4R,5S,6R)-3-azido-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-hydroxyoxan-2-yl]-1-hydroxy-2-(hydroxymethyl)but-3-yn-2-yl]carbamate
  参考文献：
  名称：

  New design concepts for constraining glycosylated amino acids

  摘要：

  In an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, two constrained glycopeptides based on the alpha -N-acetylgalactosaminyl serine substructure were chosen for synthesis. These compounds representing one of the two possible gauche conformations of the D-serine and L-serine configurations of the parent substructure were successfully prepared in reasonable overall yield through a convergent strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00545-2

文献信息

• New design concepts for constraining glycosylated amino acids
  作者：Jonathan W Lane、Randall L Halcomb

  DOI：10.1016/s0040-4020(01)00545-2

  日期：2001.7

  In an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, two constrained glycopeptides based on the alpha -N-acetylgalactosaminyl serine substructure were chosen for synthesis. These compounds representing one of the two possible gauche conformations of the D-serine and L-serine configurations of the parent substructure were successfully prepared in reasonable overall yield through a convergent strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.