(S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester | 365455-41-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[(2S,3R,4R,5R,6R)-3-nitro-5-phenylmethoxy-6-(phenylmethoxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxypropanoate
• CAS: 365455-41-0
• 化学式: C₆₆H₇₈N₂O₁₆
• 分子量: 1155.35
• InChiKey: MFGNVAQLGRMHKI-KQZIMGLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  84
• 可旋转键数：
  31
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  203
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester 在 Raney-Ni T₄ 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 生成 (S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester
  参考文献：
  名称：

  Nitroglycal Concatenation: A Broadly Applicable and Efficient Approach to the Synthesis of Complex O-Glycans

  摘要：

  Base-catalyzed glycosylations provide the basis for a new and general entry to the synthesis of mucin-type O-glycans. The desired α-linked 2-acetamidoglycosyl amino acids B are accessible selectively starting from glycals of type A. Fmoc=9-fluorenylmethoxycarbonyl.

  DOI：

  10.1002/1521-3773(20010716)40:14<2654::aid-anie2654>3.0.co;2-l
• 作为产物：
  描述：

  (2R,3R,4R)-3-Benzyloxy-2-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran 在 potassium tert-butylate 、 硝酸 、 乙酸酐 作用下， 以 甲苯 为溶剂， 生成 (S)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester
  参考文献：
  名称：

  Nitroglycal Concatenation: A Broadly Applicable and Efficient Approach to the Synthesis of Complex O-Glycans

  摘要：

  Base-catalyzed glycosylations provide the basis for a new and general entry to the synthesis of mucin-type O-glycans. The desired α-linked 2-acetamidoglycosyl amino acids B are accessible selectively starting from glycals of type A. Fmoc=9-fluorenylmethoxycarbonyl.

  DOI：

  10.1002/1521-3773(20010716)40:14<2654::aid-anie2654>3.0.co;2-l