1-(dimethylphosphonate)-2-oxo-3-(tritylamino)-5-methylhexane | 647852-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(dimethylphosphonate)-2-oxo-3-(tritylamino)-5-methylhexane
• 英文别名: (3S)-1-dimethoxyphosphoryl-5-methyl-3-(tritylamino)hexan-2-one
• CAS: 647852-06-0
• 化学式: C₂₈H₃₄NO₄P
• 分子量: 479.556
• InChiKey: SUOVUGFDYFTGRI-SANMLTNESA-N

物化性质

• 沸点：
  576.6±50.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(dimethylphosphonate)-2-oxo-3-(tritylamino)-5-methylhexane 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 、 sodium hydride 、 碳酸氢钠 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 methyl (4S,trans)-4,5-dihydro-2-isobutyl-4-phenyl-5-carboxylate
  参考文献：
  名称：

  A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates

  摘要：

  Practical synthetic routes to beta-amino-alpha-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of beta-amino-alpha-keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.009
• 作为产物：
  描述：

  L-亮氨酸 在 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(dimethylphosphonate)-2-oxo-3-(tritylamino)-5-methylhexane
  参考文献：
  名称：

  A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates

  摘要：

  Practical synthetic routes to beta-amino-alpha-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of beta-amino-alpha-keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.009

文献信息

• Proteasome selectivity towards Michael acceptor containing oligopeptide-based inhibitors
  作者：Wouter A. van der Linden、Paul P. Geurink、Chris Oskam、Gijsbert A. van der Marel、Bogdan I. Florea、Herman S. Overkleeft

  DOI：10.1039/b924134e

  日期：——

  The synthesis and biological evaluation of ten Michael acceptors containing potential proteasome inhibitors are described. Cellular targets of azide containing inhibitors Ib and VIIIb were assessed in HEK293T and RAW264.7 cells by a two step labeling strategy, followed by biotin-pulldown, affinity purification, on-bead tryptic digestion and LC-MS2 identification. This strategy appears to be an attractive alternative to gel-based competition assays.

  描述了含有潜在蛋白酶体抑制剂的十个迈克尔受体的合成与生物学评价。通过两步标记策略在HEK293T和RAW264.7细胞中评估了含有叠氮基抑制剂Ib和VIIIb的细胞内靶点，随后进行生物素-牵拉、亲和纯化、在珠上胰蛋白酶消化和LC-MS2鉴定。该策略似乎是一个有吸引力的乳胶凝胶竞争性测定的替代方案。
• A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates
  作者：Jae-Mok Lee、Hyun-Suk Lim、Kyung-Chang Seo、Sung-Kee Chung

  DOI：10.1016/j.tetasy.2003.10.009

  日期：2003.11

  Practical synthetic routes to beta-amino-alpha-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of beta-amino-alpha-keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation. (C) 2003 Elsevier Ltd. All rights reserved.