(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol | 908845-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol
• 英文别名: Mob(-2)[Mob(-3)][Mob(-6)]Glc(b1-4)[Mob(-2)][Mob(-3)][Mob(-6)]Glc(b)-N3；(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-azido-4,5-bis[(4-methoxyphenyl)methoxy]-2-[(4-methoxyphenyl)methoxymethyl]oxan-3-yl]oxy-4,5-bis[(4-methoxyphenyl)methoxy]-2-[(4-methoxyphenyl)methoxymethyl]oxan-3-ol
• CAS: 908845-58-9
• 化学式: C₆₀H₆₉N₃O₁₆
• 分子量: 1088.22
• InChiKey: WEEJJFQUWOMMGJ-CKFRCKCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  79
• 可旋转键数：
  29
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol 在 palladium on activated charcoal 、 tris(dibenzylideneacetone)dipalladium (0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 氢气 、 sodium hydride 、 sodium t-butanolate 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 126.0h， 生成
  参考文献：
  名称：

  Total synthesis of dapiramicin B

  摘要：

  The first total synthesis of dapiramicin 13, a nucleoside antibiotic, is described. The characteristic N-glycoside linkage in dapirarnicin B was effectively constructed by way of the Pd-catalyzed coupling reaction of a heptopyranosylamine with a bromo-pyrrolopyrimidine derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.001
• 作为产物：
  描述：

  (2R,4aR,6S,7R,8S,8aR)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-7,8-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine 在 4 A molecular sieve 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Total synthesis of dapiramicin B

  摘要：

  The first total synthesis of dapiramicin 13, a nucleoside antibiotic, is described. The characteristic N-glycoside linkage in dapirarnicin B was effectively constructed by way of the Pd-catalyzed coupling reaction of a heptopyranosylamine with a bromo-pyrrolopyrimidine derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.001

文献信息

• Total synthesis of dapiramicin B
  作者：Hiroyuki Ohno、Takashi Terui、Takafumi Kitawaki、Noritaka Chida

  DOI：10.1016/j.tetlet.2006.06.001

  日期：2006.8

  The first total synthesis of dapiramicin 13, a nucleoside antibiotic, is described. The characteristic N-glycoside linkage in dapirarnicin B was effectively constructed by way of the Pd-catalyzed coupling reaction of a heptopyranosylamine with a bromo-pyrrolopyrimidine derivative. (c) 2006 Elsevier Ltd. All rights reserved.