[(1R,3'R,4S,5'S,6S,7S,8S,9R,10R,12S,13S,15R,16E,18S)-15-amino-5'-[[tert-butyl(dimethyl)silyl]oxymethyl]-3'-[tert-butyl(diphenyl)silyl]oxy-8-hydroxy-16-methoxyimino-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,2'-oxolane]-10-yl] acetate | 183788-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1R,3'R,4S,5'S,6S,7S,8S,9R,10R,12S,13S,15R,16E,18S)-15-amino-5'-[[tert-butyl(dimethyl)silyl]oxymethyl]-3'-[tert-butyl(diphenyl)silyl]oxy-8-hydroxy-16-methoxyimino-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,2'-oxolane]-10-yl] acetate
• CAS: 183788-34-3
• 化学式: C₅₂H₇₈N₂O₈Si₂
• 分子量: 915.371
• InChiKey: PLWYJGWZRPCYTJ-GDQXZJPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.65
• 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：
  131
• 氢给体数：
  2
• 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,16E,18S)-15-amino-5'-[[tert-butyl(dimethyl)silyl]oxymethyl]-3'-[tert-butyl(diphenyl)silyl]oxy-8-hydroxy-16-methoxyimino-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-ene-6,2'-oxolane]-10-yl] acetate 在 polyvinylpyridine 、 4 A molecular sieve 、 二丁基二氯化锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以49%的产率得到
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/ja972160p
• 作为产物：
  描述：

  [(1R,3'R,4S,5'S,6S,7S,8S,9R,10R,12S,13S,18S)-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 吡啶 、 PTAB 、 水 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 32.0h， 生成 [(1R,3'R,4S,5'S,6S,7S,8S,9R,10R,12S,13S,15R,16E,18S)-15-amino-5'-[[tert-butyl(dimethyl)silyl]oxymethyl]-3'-[tert-butyl(diphenyl)silyl]oxy-8-hydroxy-16-methoxyimino-5',7,9,13-tetramethylspiro[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：

  Outer-Ring Stereochemical Modulation of Cytotoxicity in Cephalostatins¹

  摘要：

  [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.

  DOI：

  10.1021/ol991153y

文献信息

• An Efficient Synthesis of the C-23 Deoxy, 17α-Hydroxy South 1 Hemisphere and Its Cephalostatin 1 Analog¹
  作者：Wei Li、Philip L. Fuchs

  DOI：10.1021/ol034894e

  日期：2003.8.1

  [reaction: see text] Methods for functionalization of the D ring of diene 1 were investigated. This study led to efficient syntheses of 3 and the subsequent 23'-deoxy,17'alpha-hydroxy cephalostatin 1 analog (4). The bioactivity data of 2 and 4 are in the low nanomolar range for a 10-cell-line minipanel.

  [反应：见正文]研究了二烯1的D环官能化的方法。这项研究导致了3及其随后的23'-deoxy，17'α-hydroxycephalostatin 1类似物的有效合成（4）。对于10个细胞系的微型面板，2和4的生物活性数据处于低纳摩尔范围内。