methyl (2S)-2-(phenylmethoxycarbonylamino)-3-[(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropanoate | 329365-88-0

• 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: methyl (2S)-2-(phenylmethoxycarbonylamino)-3-[(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropanoate
• CAS: 329365-88-0
• 化学式: C₄₆H₄₉NO₁₀
• 分子量: 775.896
• InChiKey: CDZSXCDCDDJFRH-JUKPZINKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  57
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 trimethylsilyl perchlorate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 methyl (2S)-2-(phenylmethoxycarbonylamino)-3-[(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropanoate
  参考文献：
  名称：

  Catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate

  摘要：

  Catalytic and stereoselective glycosylation efficiently proceeded by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acids in the presence of a glycosyl acceptor and molecular sieves 5 angstrom. Catalytic and one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was also performed stereoselectively by the reaction with trichloroacetyl isocyanate followed by activation with a catalytic amount of activators. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.027

文献信息

• AuCl₃- and AuCl₃-Phenylacetylene-Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates
  作者：Rashmi Roy、Ashok Kumar Palanivel、Asadulla Mallick、Yashwant D. Vankar

  DOI：10.1002/ejoc.201500137

  日期：2015.6

  obtained for the glycosylation of 2-O-acetyl-protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid-sensitive nucleophiles such as Fmoc-serine tert-butyl ester or Fmoc-threonine tert-butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature.

  通过使用 AuCl3-苯乙炔中继催化剂体系进行武装和解除武装的三氯乙酰亚胺基糖基供体的糖基化。该催化体系的有效性也与单独使用 AuCl3 作为催化剂的有效性进行了比较。使用这些催化剂的糖基化在室温下在 5-45 分钟内有效进行。2-O-乙酰保护的去武装糖基供体的糖基化获得了优异的非对映选择性，而武装糖基三氯乙酰亚胺产生了异头糖苷的混合物。酸敏感性亲核试剂，如 Fmoc-丝氨酸叔丁酯或 Fmoc-苏氨酸叔丁酯，在室温温和条件下成功地进行了糖基化，尽管产率适中。
• Mukaiyama, Teruaki; Katsurada, Manabu; Takashima, Tohru, Chemistry Letters, 1991, # 6, p. 985 - 988
  作者：Mukaiyama, Teruaki、Katsurada, Manabu、Takashima, Tohru

  DOI：——

  日期：——
• Catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate
  作者：Jun-ichi Matsuo、Tatsuya Shirahata、Satoshi Ōmura

  DOI：10.1016/j.tetlet.2005.11.027

  日期：2006.1

  Catalytic and stereoselective glycosylation efficiently proceeded by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acids in the presence of a glycosyl acceptor and molecular sieves 5 angstrom. Catalytic and one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was also performed stereoselectively by the reaction with trichloroacetyl isocyanate followed by activation with a catalytic amount of activators. (c) 2005 Elsevier Ltd. All rights reserved.