(1'R,3aR,4R,6R,7aR)-N-<1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl>-2-(trimethylsilyl)ethanesulfonamide | 158413-29-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'R,3aR,4R,6R,7aR)-N-<1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl>-2-(trimethylsilyl)ethanesulfonamide
• 英文别名: N-[(1R)-1-[(3aR,4R,6R,7aR)-6-hydroxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-4-yl]-2-oxopropyl]-2-trimethylsilylethanesulfonamide
• CAS: 158413-29-7
• 化学式: C₁₇H₃₃NO₆SSi
• 分子量: 407.604
• InChiKey: GJGUVCQDTDIYOE-DGXTUMSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1'R,3aR,4R,6R,7aR)-N-<1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl>-2-(trimethylsilyl)ethanesulfonamide 在 吡啶 、 chromium(VI) oxide 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.58h， 生成 (1'R,2'S,3aR,4R,7aR)-N-<3,3-dichloro-1-(hexahydro-2,2-dimethyl-6-oxo-1,3-benzodioxol-4-yl)-2-hydroxy-2-methylpropyl>-2-(trimethylsilyl)ethanesulfonamide
  参考文献：
  名称：

  Synthetic Studies on Actinobolin and Bactobolin:  Synthesis of N-Desalanyl-N-[2-(trimethylsilyl)ethanesulfonyl] Derivatives from a Common Intermediate and Attempted Removal of the SES Protecting Group

  摘要：

  Two closely related syntheses of 5,6-O-(2-propylidene)-N-desalanyl-N-2-(trimethylsilyl)ethane-sulfonyl]bactobolin (9b) from (+)-12, an intermediate previously prepared from D-glucose, are reported. In each case, the key step involves a precedented stereoselective addition of LiCHCl2 in the presence of CeCl3 to a suitably protected a-amino ketone, Intermediates from both synthetic routes to 9b can be prepared by degradation of actinobolin (2) thereby establishing a potential method for the transformation of actinobolin into bactobolin. An efficient route to 5,6-O-(2-propylidene)-N-desalanyl-N-[[2-(trimethylsily)ethanesulfonyl]actinbolin (7b) from (+)-12 involving an unexpected cyclization of 29 was discovered. The 2-(trimethylsilyl)ethanesulfonyl (SES) protecting group in 7b tvas removed by reaction with Bu(4)NF in wet THF. The nature of the Bu(4)NF reagent was found to be important to the outcome of the reaction. Several improvements over our previously reported synthesis of actinobolin from D-glucose are noted. Although precedented, the removal of the SES protecting group from 9b could not be achieved thereby preventing completion of a total synthesis of bactobolin.

  DOI：

  10.1021/jo960579c
• 作为产物：
  描述：

  (1'R,3aR,4R,7aR)-N-<1-(hexahydro-2,2-dimethyl-6-methylene-1,3-benzodioxol-4-yl)-2-oxopropyl>-2-(trimethylsilyl)ethanesulfonamide 在 sodium tetrahydroborate 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 (1'R,3aR,4R,6R,7aR)-N-<1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl>-2-(trimethylsilyl)ethanesulfonamide
  参考文献：
  名称：

  由D-葡萄糖和（+）-肌动蛋白合成（-）-bacbolbolin

  摘要：

  由（+）- 3制备（-）- 16构成了由D-葡萄糖形式的（-）-bacbolbolin的正式对映体合成。密钥变换涉及非对映选择性加成LiCHCl的2至7中加入CeCl的存在3。已经报道了由（+）-肌动蛋白硫酸盐合成（+）- 3，并说明了（+）-肌动蛋白转化为（-）-细菌肌动蛋白。

  DOI：

  10.1016/s0040-4039(00)73216-3

文献信息

• WEINREB, STEVEN M.;GARIGIPATI, RAVI S., PURE AND APPL. CHEM., 61,(1989) N, C. 435-438
  作者：WEINREB, STEVEN M.、GARIGIPATI, RAVI S.

  DOI：——

  日期：——
• GARIGIPATI, RAVI S.;TSCHAEN, DAVID M.;WEINREB, STEVEN M., J. AMER. CHEM. SOC., 112,(1990) N, C. 3475-3482
  作者：GARIGIPATI, RAVI S.、TSCHAEN, DAVID M.、WEINREB, STEVEN M.

  DOI：——

  日期：——