(1S,2R,4aR,5R,6S,8aS)-methyl 6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-2-(hydroxymethyl)-1,5,8a-trimethyldecahydronaphthalene-1-carboxylate | 926028-72-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1S,2R,4aR,5R,6S,8aS)-methyl 6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-2-(hydroxymethyl)-1,5,8a-trimethyldecahydronaphthalene-1-carboxylate
• 英文别名: methyl (1S,2R,4aR,5R,6S,8aS)-6-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(hydroxymethyl)-1,5,8a-trimethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 926028-72-0
• 化学式: C₂₉H₅₈O₅Si₂
• 分子量: 542.948
• InChiKey: GUOVVMJRLHBEFH-ZFHJLZCFSA-N

物化性质

• 熔点：
  126-129 °C
• 沸点：
  510.9±35.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,4aR,5R,6S,8aS)-methyl 6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-2-(hydroxymethyl)-1,5,8a-trimethyldecahydronaphthalene-1-carboxylate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 以95%的产率得到(3aR,5aR,6R,7S,9aS,9bS)-7-(tert-butyldimethylsilyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-6,9a,9b-trimethyldecahydronaphtho[1,2-c]furan-1(9bH)-one
  参考文献：
  名称：

  Development of a Scalable Synthesis of a Common Eastern Tricyclic Lactone for Construction of the Nodulisporic Acids

  摘要：

  A scalable, second-generation synthesis of the densely functionalized eastern tricyclic lactone (+)-6, a common intermediate, for construction of the nodulisporic acids has been achieved. Modifications to the first-generation route now permit access to (+)-6 in 17 steps with an overall 16.5% yield. Key carbon-carbon bond constructions include a Kirk-Petrow (phenylthio)methylation, a Sc(OTf)(3)-catalyzed hydroxymethylation, a Stille carbonylation, and a Koga three-component, conjugate addition-alkylation sequence.

  DOI：

  10.1021/op060204l
• 作为产物：
  描述：

  (8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene 在 2,6-二甲基吡啶 、 盐酸 、 六甲基磷酰三胺 、 sodium chlorite 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 氨 、 草酸 、 lithium 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium chloride 、 lithium hexamethyldisilazane 、 tetramethylammonium triacetoxyborohydride 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 、 乙腈 、 叔丁醇 、 苯 为溶剂， -78.0~140.0 ℃ 、4.67 kPa 条件下， 反应 160.91h， 生成 (1S,2R,4aR,5R,6S,8aS)-methyl 6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-2-(hydroxymethyl)-1,5,8a-trimethyldecahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Development of a Scalable Synthesis of a Common Eastern Tricyclic Lactone for Construction of the Nodulisporic Acids

  摘要：

  A scalable, second-generation synthesis of the densely functionalized eastern tricyclic lactone (+)-6, a common intermediate, for construction of the nodulisporic acids has been achieved. Modifications to the first-generation route now permit access to (+)-6 in 17 steps with an overall 16.5% yield. Key carbon-carbon bond constructions include a Kirk-Petrow (phenylthio)methylation, a Sc(OTf)(3)-catalyzed hydroxymethylation, a Stille carbonylation, and a Koga three-component, conjugate addition-alkylation sequence.

  DOI：

  10.1021/op060204l

文献信息

• Nodulisporic Acid A Synthetic Studies. 2. Construction of an Eastern Hemisphere Subtarget
  作者：Amos B. Smith、Young Shin Cho、Haruaki Ishiyama

  DOI：10.1021/ol016888t

  日期：2001.11.1

  In this, the second of two Letters, we describe an effective assembly of (+)-4, an eastern hemisphere subtarget comprising the FGH rings of (+)-nodulisporic acid A (1) (17 steps, 9% overall yield). Central to the synthesis is a Koga three-component conjugate addition-alkylation sequence which secures the trans orientation of the vicinal quaternary methyl groups. [reaction: see text]

  在本文中，这是两个字母的第二个字母，我们描述了（+）-4的有效组装，这是一个包含（+）-去甲孢子酸A（1）的FGH环的东半球子目标（17个步骤，总产率为9％）。合成的中心是Koga三组分共轭加成烷基化序列，可确保邻位季甲基的反式定位。[反应：看文字]
• Development of a Scalable Synthesis of a Common Eastern Tricyclic Lactone for Construction of the Nodulisporic Acids
  作者：Amos B. Smith、László Kürti、Akin H. Davulcu、Young Shin Cho

  DOI：10.1021/op060204l

  日期：2007.1.1

  A scalable, second-generation synthesis of the densely functionalized eastern tricyclic lactone (+)-6, a common intermediate, for construction of the nodulisporic acids has been achieved. Modifications to the first-generation route now permit access to (+)-6 in 17 steps with an overall 16.5% yield. Key carbon-carbon bond constructions include a Kirk-Petrow (phenylthio)methylation, a Sc(OTf)(3)-catalyzed hydroxymethylation, a Stille carbonylation, and a Koga three-component, conjugate addition-alkylation sequence.