((2S,3R,4S)-1-hydroxy-2,4-dimethyldecan-3-yl) (S)-2-(benzyloxycarbonylamino)propanoate | 1034401-91-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ((2S,3R,4S)-1-hydroxy-2,4-dimethyldecan-3-yl) (S)-2-(benzyloxycarbonylamino)propanoate
• 英文别名: [(2S,3R,4S)-1-hydroxy-2,4-dimethyldecan-3-yl] (2S)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 1034401-91-6
• 化学式: C₂₃H₃₇NO₅
• 分子量: 407.55
• InChiKey: FYUXKTFGAJVLJP-VNYTWHDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((2S,3R,4S)-1-hydroxy-2,4-dimethyldecan-3-yl) (S)-2-(benzyloxycarbonylamino)propanoate 在 盐酸 、 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 palladium 10% on activated carbon 、 氢气 、 三氧化硫吡啶 、 1-羟基苯并三唑 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.51h， 生成 [(2R,3R,4S)-2,4-dimethyl-1-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-1-oxodecan-3-yl] (2S)-2-[[(2S)-2-[[(2S)-4-methyl-2-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]pentanoyl]amino]propanoyl]amino]propanoate
  参考文献：
  名称：

  Total synthesis of emericellamides A and B

  摘要：

  A concise total synthesis of emericellamides A and B, two cyclic depsipeptides exhibiting antibacterial and cytotoxic activities, is reported. A Paterson anti-aldol reaction and a hydroxy directed 1,3-anti reduction were applied for construction of the polypropionate unit with the required stereochemistry in emericellamides A and B. An FDPP mediated macrolactamization was used to construct the macrocycle of emericellamides A and B. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.012
• 作为产物：
  描述：

  (S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one 在 咪唑 、 4-二甲氨基吡啶 、 sodium periodate 、 palladium 10% on activated carbon 、 camphor-10-sulfonic acid 、 氯代二环己基硼烷 、 氢气 、 sodium hexamethyldisilazane 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 、 丙酮 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 21.5h， 生成 ((2S,3R,4S)-1-hydroxy-2,4-dimethyldecan-3-yl) (S)-2-(benzyloxycarbonylamino)propanoate
  参考文献：
  名称：

  Total synthesis of emericellamides A and B

  摘要：

  A concise total synthesis of emericellamides A and B, two cyclic depsipeptides exhibiting antibacterial and cytotoxic activities, is reported. A Paterson anti-aldol reaction and a hydroxy directed 1,3-anti reduction were applied for construction of the polypropionate unit with the required stereochemistry in emericellamides A and B. An FDPP mediated macrolactamization was used to construct the macrocycle of emericellamides A and B. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.012

文献信息

• The first total synthesis of emericellamide A
  作者：Subhash Ghosh、Tapan Kumar Pradhan

  DOI：10.1016/j.tetlet.2008.03.107

  日期：2008.5

  A highly convergent asymmetric total synthesis of emericellamide A, a 19-membered antibacterial depsipeptide isolated from the co-culture of an Emericella sp. (strain CNL-878) and a Salinispora arenicola (strain CNH-665) is described. (C) 2008 Elsevier Ltd. All rights reserved.
• Total synthesis of emericellamides A and B
  作者：Tapan Kumar Pradhan、Karla Mahender Reddy、Subhash Ghosh

  DOI：10.1016/j.tetasy.2013.07.012

  日期：2013.9

  A concise total synthesis of emericellamides A and B, two cyclic depsipeptides exhibiting antibacterial and cytotoxic activities, is reported. A Paterson anti-aldol reaction and a hydroxy directed 1,3-anti reduction were applied for construction of the polypropionate unit with the required stereochemistry in emericellamides A and B. An FDPP mediated macrolactamization was used to construct the macrocycle of emericellamides A and B. (C) 2013 Elsevier Ltd. All rights reserved.