(5S,7R,8S,9S)-7-Benzyloxymethyl-9-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-3-(4-methoxy-benzyl)-6-oxa-1,3-diaza-spiro[4.4]nonane-2,4-dione | 130606-96-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,7R,8S,9S)-7-Benzyloxymethyl-9-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-3-(4-methoxy-benzyl)-6-oxa-1,3-diaza-spiro[4.4]nonane-2,4-dione
• 英文别名: (5S,7R,8S,9S)-9-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-3-[(4-methoxyphenyl)methyl]-7-(phenylmethoxymethyl)-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione
• CAS: 130606-96-1
• 化学式: C₂₈H₃₈N₂O₇Si
• 分子量: 542.704
• InChiKey: VQZIINRJGVPMBT-DELVEFKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5S,7R,8S,9S)-7-Benzyloxymethyl-9-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-3-(4-methoxy-benzyl)-6-oxa-1,3-diaza-spiro[4.4]nonane-2,4-dione 在 palladium on activated charcoal ammonium cerium(IV) nitrate 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 生成 <2R,3R,4R,5S>-3,4-Dihydroxy-2-hydroxymethyl-6,8-diaza-1-oxaspiro<4.4>nonane-7,9-dione
  参考文献：
  名称：

  Synthetic studies on (+)-hydantocidin (2): Aldol addition approaches toward the stereoisomers of (+)-hydantocidin

  摘要：

  The spiro-hydantoin ring at the anomeric position of D-and L-furanose was constructed by using aldol addition followed by acid promoted cyclization and the synthesis of thestereoisomers of (+)-hydantocidin, L- and D-series of spiro-furanose 2, 3, 4 and 5.

  DOI：

  10.1016/s0040-4020(01)96123-x
• 作为产物：
  描述：

  <5R,1'R,2'R,3'S>-5-(1'-t-Butyldimethylsilyloxy-2',3'-O-isopropylidenedioxy-4'-benzyloxy)butyl-5-methoxy-3-(4-methoxybenzyl)-1-N-methoxycarbonylhydantoin 在 potassium carbonate 、 对甲苯磺酸 、 乙二醇 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 (5S,7R,8S,9S)-7-Benzyloxymethyl-9-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-3-(4-methoxy-benzyl)-6-oxa-1,3-diaza-spiro[4.4]nonane-2,4-dione
  参考文献：
  名称：

  Synthetic studies on (+)-hydantocidin (2): Aldol addition approaches toward the stereoisomers of (+)-hydantocidin

  摘要：

  The spiro-hydantoin ring at the anomeric position of D-and L-furanose was constructed by using aldol addition followed by acid promoted cyclization and the synthesis of thestereoisomers of (+)-hydantocidin, L- and D-series of spiro-furanose 2, 3, 4 and 5.

  DOI：

  10.1016/s0040-4020(01)96123-x

文献信息

• Synthetic studies on (+)-hydantocidin (4): Synthesis of stereoisomers of (+)-hydantocidin
  作者：Shigeru Mio、Masumi Ueda、Masae Hamura、Junko Kitagawa、Soji Sugai

  DOI：10.1016/s0040-4020(01)96125-3

  日期：——

  The stereoisomers of (+)-hydantocidin were synthesized by diastereoselective dihydroxylation directly or epoxidation followed by ring opening of 1-oxa-6,8-diazaspiro[4.4]nonane-3-ene-7,9-dione systems.