(E)-(2R,3S,4R,6R)-2-[(4R,5R,6R)-2,2-Di-tert-butyl-5-methyl-6-((S)-1-methyl-2-oxo-butyl)-[1,3,2]dioxasilinan-4-yl]-3-hydroxy-4,6,8-trimethyl-undec-8-en-5-one | 165547-40-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-(2R,3S,4R,6R)-2-[(4R,5R,6R)-2,2-Di-tert-butyl-5-methyl-6-((S)-1-methyl-2-oxo-butyl)-[1,3,2]dioxasilinan-4-yl]-3-hydroxy-4,6,8-trimethyl-undec-8-en-5-one
• 英文别名: (E,2R,3S,4R,6R)-2-[(4R,5R,6R)-2,2-ditert-butyl-5-methyl-6-[(2S)-3-oxopentan-2-yl]-1,3,2-dioxasilinan-4-yl]-3-hydroxy-4,6,8-trimethylundec-8-en-5-one
• CAS: 165547-40-0
• 化学式: C₃₁H₅₈O₅Si
• 分子量: 538.884
• InChiKey: ZTEUIGGWJGLVGY-JDSZWMJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.65
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(2R,3S,4R,6R)-2-[(4R,5R,6R)-2,2-Di-tert-butyl-5-methyl-6-((S)-1-methyl-2-oxo-butyl)-[1,3,2]dioxasilinan-4-yl]-3-hydroxy-4,6,8-trimethyl-undec-8-en-5-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (E,2S,4S,6R)-2-[(4S,5S,6R)-2,2-ditert-butyl-5-methyl-6-[(2S)-3-oxopentan-2-yl]-1,3,2-dioxasilinan-4-yl]-4,6,8-trimethylundec-8-ene-3,5-dione
  参考文献：
  名称：

  Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

  摘要：

  The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C-4-C-8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00617-0
• 作为产物：
  描述：

  二叔丁基硅基双(三氟甲烷磺酸) 在 2,6-二甲基吡啶 、 mercury(II) perchlorate 、 iron(III)-acetylacetonate 、 phosphate buffer pH 7.4 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 14.08h， 生成 (E)-(2R,3S,4R,6R)-2-[(4R,5R,6R)-2,2-Di-tert-butyl-5-methyl-6-((S)-1-methyl-2-oxo-butyl)-[1,3,2]dioxasilinan-4-yl]-3-hydroxy-4,6,8-trimethyl-undec-8-en-5-one
  参考文献：
  名称：

  Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

  摘要：

  The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C-4-C-8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00617-0

文献信息

• Asymmetric synthesis of (−)-denticulatins A and B via group-selective aldolization of a meso dialdehyde with a chiral N-propionylsultam
  作者：Wolfgang Oppolzer、Jef De Brabander、Eric Walther、Gérald Bernardinelli

  DOI：10.1016/0040-4039(95)00787-d

  日期：1995.6

  Aldolization of meso dialdehyde 3 with a borylenolate obtained from chiral N-propionylsultam 4 yields efficiently lactols 5 with simultaneous generation of five stereogenic centers.Dithioketalization/O-desilylation of 5 affords acyclic diol 9 which is converted into the marine polypropionates 1a and 1bvia the asymmetric alkylation of N-propionyltoluenesultam 11 and the aldol coupling 10 + 15 → 16.

  的醛醇缩合内消旋二醛3与手性获得的borylenolate Ñ -propionylsultam 4倍的产率有效地乳醇5与同时产生的5立构centers.Dithioketalization / ø -desilylation的5得到无环二醇9被转换为海洋聚丙1A和1B通过在N-丙酰基甲苯磺酰胺11的不对称烷基化和羟醛偶联10 + 15→16。
• Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step
  作者：Jef De Brabander、Wolfgang Oppolzer

  DOI：10.1016/s0040-4020(97)00617-0

  日期：1997.7

  The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C-4-C-8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield. (C) 1997 Elsevier Science Ltd.