[(1R,3'R,4S,5'S,6S,7S,8S,9R,10R,12S,13S,15R,18S)-15-azido-5'-[[tert-butyl(dimethyl)silyl]oxymethyl]-3'-[tert-butyl(diphenyl)silyl]oxy-8-hydroxy-5',7,9,13-tetramethyl-16-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,2'-oxolane]-10-yl] acetate | 170510-32-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(1R,3'R,4S,5'S,6S,7S,8S,9R,10R,12S,13S,15R,18S)-15-azido-5'-[[tert-butyl(dimethyl)silyl]oxymethyl]-3'-[tert-butyl(diphenyl)silyl]oxy-8-hydroxy-5',7,9,13-tetramethyl-16-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,2'-oxolane]-10-yl] acetate
• CAS: 170510-32-4
• 化学式: C₅₁H₇₃N₃O₈Si₂
• 分子量: 912.327
• InChiKey: JJPAZOKSYCNGKA-YAWCSKADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.57
• 重原子数：
  64
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1R,3'R,4S,5'S,6S,7S,8S,9R,10R,12S,13S,15R,18S)-15-azido-5'-[[tert-butyl(dimethyl)silyl]oxymethyl]-3'-[tert-butyl(diphenyl)silyl]oxy-8-hydroxy-5',7,9,13-tetramethyl-16-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,2'-oxolane]-10-yl] acetate 在 sodium hydrogen telluride 、 air 、 "North Azidoketone" C51H73N3O8Si2 、 silica gel 作用下， 生成
  参考文献：
  名称：

  Jeong, Jae Uk; Sutton, Scott C.; Kim, Seongkon, Journal of the American Chemical Society, 1995, vol. 117, # 40, p. 10157 - 10158

  摘要：

  DOI：
• 作为产物：
  描述：

  在 咪唑 、 PTAB 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 11.0h， 生成 [(1R,3'R,4S,5'S,6S,7S,8S,9R,10R,12S,13S,15R,18S)-15-azido-5'-[[tert-butyl(dimethyl)silyl]oxymethyl]-3'-[tert-butyl(diphenyl)silyl]oxy-8-hydroxy-5',7,9,13-tetramethyl-16-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,2'-oxolane]-10-yl] acetate
  参考文献：
  名称：

  从 Hecogenin Acetate1 合成头孢抑素家族的 North 1 单元

  摘要：

  Hecogenin 醋酸盐 (1) 转化为 North 1 叠氮酮 5，涉及几个关键转化：(1) 通过 Reich iodoso 烯化将环硫酸盐 33b 转化为烯丙醇 40；(2) 通过高度官能化仲醇 40 的分子间氧烷基化，使用 α-重氮膦酰基乙酸酯的铑催化分解生成 α-烷氧基膦酰基乙酸酯 52，随后进行分子内 Wadsworth-Emmons 反应生成烷氧基二氢呋喃 53；(3) 通过铬 (II) 将叔溴化物 86 还原成 9:1 的非对映螺缩酮 90α/90β 混合物建立 C20 立体化学，分离为甲硅烷基醚 91α/91β。91α 向 α-叠氮酮 5 的转化很顺利。

  DOI：

  10.1021/ja9817139

文献信息

• Interphylal Product Splicing:  The First Total Syntheses of Cephalostatin 1, the North Hemisphere of Ritterazine G, and the Highly Active Hybrid Analogue, Ritterostatin G_N1_N¹
  作者：Thomas G. LaCour、Chuangxing Guo、Sudhakar Bhandaru、Michael R. Boyd、P. L. Fuchs

  DOI：10.1021/ja972160p

  日期：1998.2.1

  Convergent total syntheses of the extremely potent cell growth inhibitor cephalostatin 1 and two hybrid analogues, ritterostatins G(N)1(N) and G(N)1(S), have been achieved. Ritterostatin G(N)1(N) displays sub-nanomolar activity in the 60 cell line human tumor panel of the National Cancer Institute. The North hemisphere of ritterazine G was efficiently constructed from hecogenin acetate in 15% yield over 13 steps. Extension of a key photolysis/Prins sequence to intermediates 19 and 32 proceeded in excellent yield, leading to installation of the Delta(14) moiety in the-North G-and South I steroidal subunits. Application of a method for directed unsymmetrical coupling furnished the natural and analogue pyrazines in good yield from the cephalostatin and ritterazine components.
• Outer-Ring Stereochemical Modulation of Cytotoxicity in Cephalostatins¹
  作者：Thomas G. LaCour、Chuangxing Guo、Michael R. Boyd、Philip L. Fuchs

  DOI：10.1021/ol991153y

  日期：2000.1.1

  [GRAPHICS]20- and 25'-epimers of cephalostatin 7, prepared by directed unsymmetrical pyrazine synthesis, address outer-ring topographical and stability questions and intimate an oxacarbenium ion rationale for the role in bioactivity of the spiroketal (E/F, E'/F') rings of this class of antitumor agents.