(5R,6R)-5-(Boc-amino)-6-methyl-5,6-dihydropyran-2-one | 191013-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (5R,6R)-5-(Boc-amino)-6-methyl-5,6-dihydropyran-2-one
• 英文别名: tert-butyl N-[(2R,3R)-2-methyl-6-oxo-2,3-dihydropyran-3-yl]carbamate
• CAS: 191013-81-7
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: SWQQVXPWXDNYLZ-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,6R)-5-(Boc-amino)-6-methyl-5,6-dihydropyran-2-one 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 以73%的产率得到tert-butyl N-[(2R,3R,4R,5R)-4,5-dihydroxy-2-methyl-6-oxooxan-3-yl]carbamate
  参考文献：
  名称：

  A new access to enantiomerically pure deoxy aminohexoses: Methyl 4-amino-4,6-dideoxygulopyranoside and epi-tolyposamine

  摘要：

  New efficient synthetic routes have been developed starting from the fully protected L-threonine derivative 1 for some deoxy-4-aminohexoses: methyl 4-amino-4,6-dideoxy gulopyranoside 2 and epi-tolyposamine 3. The title compounds were synthesized using an improved Horner-Emmons reaction of the threonine derived aldehyde 7. A new method for selective removal of the aminal protection is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00304-9
• 作为产物：
  描述：

  BOC-苏氨酸甲酯 在 18-冠醚-6 、 三氟化硼乙醚 、 二异丁基氢化铝 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 144.41h， 生成 (5R,6R)-5-(Boc-amino)-6-methyl-5,6-dihydropyran-2-one
  参考文献：
  名称：

  A new access to enantiomerically pure deoxy aminohexoses: Methyl 4-amino-4,6-dideoxygulopyranoside and epi-tolyposamine

  摘要：

  New efficient synthetic routes have been developed starting from the fully protected L-threonine derivative 1 for some deoxy-4-aminohexoses: methyl 4-amino-4,6-dideoxy gulopyranoside 2 and epi-tolyposamine 3. The title compounds were synthesized using an improved Horner-Emmons reaction of the threonine derived aldehyde 7. A new method for selective removal of the aminal protection is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00304-9

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。