benzyl N-[(1R)-2-oxo-1-[(2R,3R)-3-[(1R)-2-oxo-1-(phenylmethoxycarbonylamino)ethyl]-1,4-dioxaspiro[4.5]decan-2-yl]ethyl]carbamate | 1053711-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-[(1R)-2-oxo-1-[(2R,3R)-3-[(1R)-2-oxo-1-(phenylmethoxycarbonylamino)ethyl]-1,4-dioxaspiro[4.5]decan-2-yl]ethyl]carbamate
• CAS: 1053711-13-9
• 化学式: C₂₈H₃₂N₂O₈
• 分子量: 524.571
• InChiKey: FNGRLTFEYUIPBM-CXSMSNRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl N-[(1R)-2-oxo-1-[(2R,3R)-3-[(1R)-2-oxo-1-(phenylmethoxycarbonylamino)ethyl]-1,4-dioxaspiro[4.5]decan-2-yl]ethyl]carbamate 在 2 、 sodium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol
  参考文献：
  名称：

  Synthesis of 1,4-Diaminocyclitols From l-Serine Methyl Ester

  摘要：

  L-Serine methyl ester hydrochloride was converted to (S)-2-[N-(benzyloxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)propanal (6). Homocoupling of 6 promoted by [V2Cl3(THF)(6)](2)[Zn2Cl6] (1) gave C-2-symmetric diol (7). After manipulation of protecting groups and Swern oxidation, 7 was converted to a 1,6-dialdehyde 10. Intramolecular pinacol coupling of 10 with 1 gave a selectively protected 1,4-diamino-2,3,5,6-tetrahydroxycyclohexane, which is the key skeleton of Fortimicin AM and AK.

  DOI：

  10.1021/jo960691a
• 作为产物：
  描述：

  N-苄氧羰酰基-L-丝氨酸甲酯 在 咪唑 、 sodium tetrahydroborate 、 草酰氯 、 2 、 四丁基氟化铵 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 calcium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 17.75h， 生成 benzyl N-[(1R)-2-oxo-1-[(2R,3R)-3-[(1R)-2-oxo-1-(phenylmethoxycarbonylamino)ethyl]-1,4-dioxaspiro[4.5]decan-2-yl]ethyl]carbamate
  参考文献：
  名称：

  Synthesis of 1,4-Diaminocyclitols From l-Serine Methyl Ester

  摘要：

  L-Serine methyl ester hydrochloride was converted to (S)-2-[N-(benzyloxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)propanal (6). Homocoupling of 6 promoted by [V2Cl3(THF)(6)](2)[Zn2Cl6] (1) gave C-2-symmetric diol (7). After manipulation of protecting groups and Swern oxidation, 7 was converted to a 1,6-dialdehyde 10. Intramolecular pinacol coupling of 10 with 1 gave a selectively protected 1,4-diamino-2,3,5,6-tetrahydroxycyclohexane, which is the key skeleton of Fortimicin AM and AK.

  DOI：

  10.1021/jo960691a

文献信息

• Synthesis of 1,4-Diaminocyclitols From <scp>l</scp>-Serine Methyl Ester
  作者：Min Kang、Jeonghan Park、Andrei W. Konradi、Steven F. Pedersen

  DOI：10.1021/jo960691a

  日期：1996.1.1

  L-Serine methyl ester hydrochloride was converted to (S)-2-[N-(benzyloxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)propanal (6). Homocoupling of 6 promoted by [V2Cl3(THF)(6)](2)[Zn2Cl6] (1) gave C-2-symmetric diol (7). After manipulation of protecting groups and Swern oxidation, 7 was converted to a 1,6-dialdehyde 10. Intramolecular pinacol coupling of 10 with 1 gave a selectively protected 1,4-diamino-2,3,5,6-tetrahydroxycyclohexane, which is the key skeleton of Fortimicin AM and AK.