4-(N-tert-butoxycarbonyl)amino-4-deoxy-1,2,3-tri-O-tert-butyldimethylsilyl-D-ribitol | 620960-70-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-(N-tert-butoxycarbonyl)amino-4-deoxy-1,2,3-tri-O-tert-butyldimethylsilyl-D-ribitol
• 英文别名: tert-butyl N-[(2R,3R,4S)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-1-hydroxypentan-2-yl]carbamate
• CAS: 620960-70-5
• 化学式: C₂₈H₆₃NO₆Si₃
• 分子量: 594.068
• InChiKey: AWODUNTXECBLBT-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(N-tert-butoxycarbonyl)amino-4-deoxy-1,2,3-tri-O-tert-butyldimethylsilyl-D-ribitol 在 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium azide 、 camphor-10-sulfonic acid 、 sodium perchlorate 、 四丁基氟化铵 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 caesium carbonate 、 三乙胺 、 三氟乙酸 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 碳酸氢钠 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (S)-2-{(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-dihydroxy-pentanoylamino}-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and structural revision of eurypamides isolated from the Palauan sponge Microciona eurypa

  摘要：

  Eurypamides A and B, 1 and 2, were successfully synthesized by employing Tl(NO3)(3) (TTN) oxidation of the corresponding halogenated phenols, 9, 16, and 26. This investigation revealed that the dihydroxyarginine residue of 1 should be revised to possess (2S,3R,4S)-configuration. In addition, the synthesis of 2 provided a pure sample, which was previously characterized in a mixture. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.105
• 作为产物：
  描述：

  2,3,5-tri-O-benzyl-1-O-tert-butyldimethylsilyl-4-O-p-nitrobenzoyl-L-lyxitol 在 palladium dihydroxide 吡啶 、 2,6-二甲基吡啶 、 二苯基磷酸 、 水 、 氢气 、 sodium methylate 、 二异丁基氢化铝 、 碳酸氢钠 、 三苯基膦 、 calcium carbonate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 4-(N-tert-butoxycarbonyl)amino-4-deoxy-1,2,3-tri-O-tert-butyldimethylsilyl-D-ribitol
  参考文献：
  名称：

  Synthesis and structural revision of eurypamides isolated from the Palauan sponge Microciona eurypa

  摘要：

  Eurypamides A and B, 1 and 2, were successfully synthesized by employing Tl(NO3)(3) (TTN) oxidation of the corresponding halogenated phenols, 9, 16, and 26. This investigation revealed that the dihydroxyarginine residue of 1 should be revised to possess (2S,3R,4S)-configuration. In addition, the synthesis of 2 provided a pure sample, which was previously characterized in a mixture. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.105

文献信息

• Total synthesis of eurypamides, marine cyclic-isodityrosines from the Palauan sponge Microciona eurypa
  作者：Miyuki Ito、Maki Yamanaka、Noriki Kutsumura、Shigeru Nishiyama

  DOI：10.1016/j.tet.2004.04.062

  日期：2004.6

  Total synthesis of eurypamides A, B, and D, 1, 2, and 4, has been successfully accomplished. The Tl(NO3)(3) (TTN) oxidation of the halogenated bisphenols, 14a, 14b, 24, and 43, effected regio-controlled cyclization to provide the corresponding diaryl ethers, 15a, 15b, 25, and 46. This investigation revealed a structural revision of eurypamide A as to possess (2"S,3"R,4"S)-configuration (47), along with the spectral data of pure 2 and 4, which were previously characterized in a mixture. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and structural revision of eurypamides isolated from the Palauan sponge Microciona eurypa
  作者：Miyuki Ito、Maki Yamanaka、Noriki Kutsumura、Shigeru Nishiyama

  DOI：10.1016/j.tetlet.2003.08.105

  日期：2003.10

  Eurypamides A and B, 1 and 2, were successfully synthesized by employing Tl(NO3)(3) (TTN) oxidation of the corresponding halogenated phenols, 9, 16, and 26. This investigation revealed that the dihydroxyarginine residue of 1 should be revised to possess (2S,3R,4S)-configuration. In addition, the synthesis of 2 provided a pure sample, which was previously characterized in a mixture. (C) 2003 Elsevier Ltd. All rights reserved.