(2S,3R,4S,5S,6S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-6-[1,3]dithiolan-2-yl-3,5-dihydroxy-2,4-dimethyl-heptan-1-one | 165547-36-4

• 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: (2S,3R,4S,5S,6S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-6-[1,3]dithiolan-2-yl-3,5-dihydroxy-2,4-dimethyl-heptan-1-one
• 英文别名: (2S,3R,4S,5S,6S)-1-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-6-(1,3-dithiolan-2-yl)-3,5-dihydroxy-2,4-dimethylheptan-1-one；(2S,3R,4S,5S,6S)-1-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-6-(1,3-dithiolan-2-yl)-3,5-dihydroxy-2,4-dimethylheptan-1-one
• CAS: 165547-36-4
• 化学式: C₂₂H₃₇NO₅S₃
• 分子量: 491.737
• InChiKey: XFKJAQFGPXIDIV-MNGXECRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-6-[1,3]dithiolan-2-yl-3,5-dihydroxy-2,4-dimethyl-heptan-1-one 在 2,6-二甲基吡啶 、 mercury(II) perchlorate 、 phosphate buffer pH 7.4 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 19.25h， 生成 (+)-camphorsultam
  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：

  (3S,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-1-methyl-2-oxo-ethyl]-3,5-dimethyl-tetrahydro-pyran-2-one 在 二异丁基氢化铝 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S,3R,4S,5S,6S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-6-[1,3]dithiolan-2-yl-3,5-dihydroxy-2,4-dimethyl-heptan-1-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.