tert-butyl-[(3S,6R)-6-[(4R,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-3-(methoxymethoxy)-6-phenylsulfanylhex-4-ynoxy]-diphenylsilane | 1477482-23-7

• 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: tert-butyl-[(3S,6R)-6-[(4R,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-3-(methoxymethoxy)-6-phenylsulfanylhex-4-ynoxy]-diphenylsilane
• CAS: 1477482-23-7
• 化学式: C₄₃H₅₂O₆SSi
• 分子量: 725.034
• InChiKey: BVTBFBAMYHFQGW-PXKGFRMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(3S,6R)-6-[(4R,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-3-(methoxymethoxy)-6-phenylsulfanylhex-4-ynoxy]-diphenylsilane 在 甲巯咪唑 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 3.25h， 生成
  参考文献：
  名称：

  Stereoselective Synthesis of the C13-C28 Subunit of (-)-Laulimalide Utilizing an α-Chlorosulfide Intermediate

  摘要：

  A stereoselective route to the C13-C28 subunit of (-)-laulimalide is described. l-Tartaric acid is the source of the hydroxy groups at C19 and C20. An -chlorosulfide is employed as the key intermediate for the creation of the C17-C18 bond and the C16-C17 double bond was introduced using the Mislow-Braverman rearrangement and Hutchin's dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans-disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia-Kocienski olefination reaction, respectively.

  DOI：

  10.1055/s-0033-1339493
• 作为产物：
  描述：

  3-(tert-butyldiphenylsilyloxy)-1-propanal 在 titanium(IV) isopropylate 、 lithium chloro-isopropyl-magnesium chloride 、 diethylzinc 、 (R)-1,1'-Bi-2-naphthol 、 四丁基碘化铵 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 33.17h， 生成 tert-butyl-[(3S,6R)-6-[(4R,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-3-(methoxymethoxy)-6-phenylsulfanylhex-4-ynoxy]-diphenylsilane
  参考文献：
  名称：

  Stereoselective Synthesis of the C13-C28 Subunit of (-)-Laulimalide Utilizing an α-Chlorosulfide Intermediate

  摘要：

  A stereoselective route to the C13-C28 subunit of (-)-laulimalide is described. l-Tartaric acid is the source of the hydroxy groups at C19 and C20. An -chlorosulfide is employed as the key intermediate for the creation of the C17-C18 bond and the C16-C17 double bond was introduced using the Mislow-Braverman rearrangement and Hutchin's dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans-disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia-Kocienski olefination reaction, respectively.

  DOI：

  10.1055/s-0033-1339493

文献信息

• Stereoselective Synthesis of the C13-C28 Subunit of (-)-Laulimalide Utilizing an α-Chlorosulfide Intermediate
  作者：Sadagopan Raghavan、Pradip Samanta

  DOI：10.1055/s-0033-1339493

  日期：——

  A stereoselective route to the C13-C28 subunit of (-)-laulimalide is described. l-Tartaric acid is the source of the hydroxy groups at C19 and C20. An -chlorosulfide is employed as the key intermediate for the creation of the C17-C18 bond and the C16-C17 double bond was introduced using the Mislow-Braverman rearrangement and Hutchin's dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans-disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia-Kocienski olefination reaction, respectively.