(R)-dimethyl (3-((tert-butyldimethylsilyl)oxy)-2-oxobutyl)phosphonate | 874384-04-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (R)-dimethyl (3-((tert-butyldimethylsilyl)oxy)-2-oxobutyl)phosphonate
• 英文别名: (R)-dimethyl 2-(tert-butyldimethylsilyloxy)-1-oxopropyl phosphonate；(R)-dimethyl 3-(tert-butyldimethylsilyloxy)-2-oxobutylphosphonate；(3R)-3-[tert-butyl(dimethyl)silyl]oxy-1-dimethoxyphosphorylbutan-2-one
• CAS: 874384-04-0
• 化学式: C₁₂H₂₇O₅PSi
• 分子量: 310.403
• InChiKey: ZXGFLFSPUGLBJD-SNVBAGLBSA-N

物化性质

• 沸点：
  331.6±27.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-dimethyl (3-((tert-butyldimethylsilyl)oxy)-2-oxobutyl)phosphonate 在 palladium dihydroxide 氢气 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 甲醇 、 乙腈 为溶剂， 20.0 ℃ 、607.95 kPa 条件下， 反应 84.0h， 生成 (2S,9R)-2-amino-9-(tert-butyldimethylsilyloxy)-8-oxodecanoic acid
  参考文献：
  名称：

  Synthesis of 2-Amino-8-oxodecanoic Acids (Aodas) Present in Natural Hystone Deacetylase Inhibitors

  摘要：

  Differently substituted 2-amino-8-oxodecanoic acids (Aodas), present in naturally occurring inhibitors of hystone deacetylase (HDAC), have been prepared using a convergent approach. The configuration in position 2 was derived from enantiomerically pure allylglycine or glutamic acid, whereas the stereochemistry of the substituent in position 9 derived from lactic acid or glyceraldehyde derivatives. Starting from allylglycine, (S)-Aodas, protected at the nitrogen as Boc or Fmoc, were obtained in four steps in about 30% overall yield. These products have been used to prepare a simplified analogue of a natural cyclic tetrapeptide HDAC inhibitor by SPPS.

  DOI：

  10.1021/jo0518250
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-dimethyl (3-((tert-butyldimethylsilyl)oxy)-2-oxobutyl)phosphonate
  参考文献：
  名称：

  十元内酯的发散合成：Aspinolides C、F、G、H 和 I

  摘要：

  在此，我们报告了十元内酯 aspinolides C、F、G、H 和 I 的合成。Aspinolides F-I 是通过将合适的醇或羧酸立体选择性地 1,4-加成到 aspinolide C 上合成的，它是由 aspinolide B 中的烯丙醇化学选择性氧化制备的。1,4-加成反应的立体选择性可以使用涉及十元内酯系统的外围攻击模型合理化。使用亚异丙基-d-核糖作为起始原料，分 11 个步骤制备 Aspinolide C，总收率为 14% 。

  DOI：

  10.1016/j.tet.2023.133449

文献信息

• Total synthesis of marine natural products separacenes A and B
  作者：Subhendu Das、Rajib Kumar Goswami

  DOI：10.1039/c7ob00345e

  日期：——

  A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl D-lactate and D-(−)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost–Rychnovsky alkyne rearrangement to construct the C7–C9 conjugated diene, the Horner–Wadsworth–Emmons olefination to form the C5–C6 and C11–C12 olefins and

  已经使用（+）-甲基D-乳酸酯和D -（-）-酒石酸作为手性库，开发了短间隔且收敛的立体异构全合成Separacenes A和B的途径。该合成的特征包括Trost–Rychnovsky炔重排以构建C 7 –C 9共轭二烯，Horner–Wadsworth–Emmons烯烃化以形成C 5 –C 6和C 11 –C 12烯烃以及Corey– Bakshi–Shibata反应安装C-13羟基官能团。
• Total synthesis of a piperidine alkaloid, microcosamine A
  作者：Chada Raji Reddy、Bellamkonda Latha、Kamalkishor Warudikar、Kiran Kumar Singarapu

  DOI：10.1039/c5ob02085a

  日期：——

  The first total synthesis of a novel piperidine alkaloid, microcosamine A, is achieved from commercially available d-serine, d-methyl lactate and 1-octyne as starting materials.

  首次成功从商业可获得的D-丝氨酸、D-甲基乳酸酯和1-辛烯作为起始物质，合成了一种新型哌啶生物碱微孔胺A。
• Stem Cell Culture Methods
  申请人：Adams David Roger

  公开号：US20120202287A1

  公开（公告）日：2012-08-09

  The invention provides methods for reversibly inhibiting stem cell differentiation wherein a compound of formula (I) is contacted with a stem cell. The invention further provides a method for preparing a culture medium, a culture medium supplement and a composition comprising a compound of formula (I).

  本发明提供了可逆地抑制干细胞分化的方法，其中化合物(I)的配制与干细胞接触。本发明还提供了制备培养基、培养基补充剂和包含化合物(I)的组合物的方法。
• Total Synthesis, NMR Solution Structure, and Binding Model of the Potent Histone Deacetylase Inhibitor FR235222
  作者：Manuela Rodriquez、Stefania Terracciano、Elena Cini、Giulia Settembrini、Ines Bruno、Giuseppe Bifulco、Maurizio Taddei、Luigi Gomez-Paloma

  DOI：10.1002/anie.200501995

  日期：2006.1.9
• Synthesis of 2-Amino-8-oxodecanoic Acids (Aodas) Present in Natural Hystone Deacetylase Inhibitors
  作者：Manuela Rodriquez、Ines Bruno、Elena Cini、Mauro Marchetti、Maurizio Taddei、Luigi Gomez-Paloma

  DOI：10.1021/jo0518250

  日期：2006.1.1

  Differently substituted 2-amino-8-oxodecanoic acids (Aodas), present in naturally occurring inhibitors of hystone deacetylase (HDAC), have been prepared using a convergent approach. The configuration in position 2 was derived from enantiomerically pure allylglycine or glutamic acid, whereas the stereochemistry of the substituent in position 9 derived from lactic acid or glyceraldehyde derivatives. Starting from allylglycine, (S)-Aodas, protected at the nitrogen as Boc or Fmoc, were obtained in four steps in about 30% overall yield. These products have been used to prepare a simplified analogue of a natural cyclic tetrapeptide HDAC inhibitor by SPPS.