<3R,4S,5R,6S,7S,8S>-1-<<(tert-butyldiphenyl)silyl>oxy>-6-<2-<<(tert-butyldiphenyl)silyl>oxy>ethyl>-10-<(N,N-diisopropyl)carbamate>-4,8-dimethyl-3,5,7-trihydroxydeca-9-ene | 220366-11-0

• 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: <3R,4S,5R,6S,7S,8S>-1-<<(tert-butyldiphenyl)silyl>oxy>-6-<2-<<(tert-butyldiphenyl)silyl>oxy>ethyl>-10-<(N,N-diisopropyl)carbamate>-4,8-dimethyl-3,5,7-trihydroxydeca-9-ene
• CAS: 220366-11-0
• 化学式: C₅₃H₇₇NO₇Si₂
• 分子量: 896.368
• InChiKey: GNHWLSXRZOFXPI-GFEQFICRSA-N

物化性质

• 沸点：
  842.358±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.097±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.66
• 重原子数：
  63.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  108.69
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  <3R,4S,5R,6S,7S,8S>-1-<<(tert-butyldiphenyl)silyl>oxy>-6-<2-<<(tert-butyldiphenyl)silyl>oxy>ethyl>-10-<(N,N-diisopropyl)carbamate>-4,8-dimethyl-3,5,7-trihydroxydeca-9-ene 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 <2S,3R,4R,5R,6R(1S,2R)>-5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-<(tert-butyldiphenylsilyl)oxy>-3-hydroxypent-2-yl>-3-methyltetrahydropyran-2,4-diol 、 <2R,3R,4R,5R,6R(1S,2R)>-5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-<(tert-butyldiphenylsilyl)oxy>-3-hydroxypent-2-yl>-3-methyltetrahydropyran-2,4-diol
  参考文献：
  名称：

  Allyltitanates in Stereospecific Additions to Chiral δ-Lactol:  Efficient Enantioselective Route to a Potential Precursor of the C1−C9 Portion of Tylonolide

  摘要：

  The Hoppe reaction, which is an allylation reaction of aldehydes using an optically active titanated crotyl carbamate intermediate generated from the corresponding N,N-diisopropyl crotyl carbamate with n-BuLi/(-)-sparteine, was in most cases applied to achiral aldehydes. In this work an extension of this reaction is reported using a racemic gamma-alkoxy allyltitanate (17) and an optically active aldehyde (16) to deliver in good yield the anti adduct 18 as the major isomer. When the corresponding delta-lactol 24 was used in place of aldehyde 16, the anti adduct 25 was obtained in 94% yield as the only product. Structural modifications effected on 25 delivered aldehyde 28 which was in turn submitted to a second allylation reaction in the presence of the optically active titanated crotyl carbamate 2, prepared as described by Hoppe from crotyl carbamate 1, to conduct to compound 29 in 80% yield. This derivative corresponds to a potential precursor of the C1-C9 portion of Tylonolide, aglycon of Tylosin (4).

  DOI：

  10.1021/jo9807722
• 作为产物：
  描述：

  <4R,5S,6R(3S,4S,5S)<2R/S-(2-tetrahydropyranyl)oxy>>-4-(<2-<(tert-butyldimethyl)silyl>oxy>ethyl)-6-<(7-<(N,N-diisopropyl)carbamate>-4-hydroxy-5-methyl-1-<<(2-tetrahydropyranyl)oxy>>hept-6-en)-3-yl>-2,2,5-trimethyl<1,3>dioxane 在 咪唑 、 Amberlyst H+ 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 <3R,4S,5R,6S,7S,8S>-1-<<(tert-butyldiphenyl)silyl>oxy>-6-<2-<<(tert-butyldiphenyl)silyl>oxy>ethyl>-10-<(N,N-diisopropyl)carbamate>-4,8-dimethyl-3,5,7-trihydroxydeca-9-ene
  参考文献：
  名称：

  Allyltitanates in Stereospecific Additions to Chiral δ-Lactol:  Efficient Enantioselective Route to a Potential Precursor of the C1−C9 Portion of Tylonolide

  摘要：

  The Hoppe reaction, which is an allylation reaction of aldehydes using an optically active titanated crotyl carbamate intermediate generated from the corresponding N,N-diisopropyl crotyl carbamate with n-BuLi/(-)-sparteine, was in most cases applied to achiral aldehydes. In this work an extension of this reaction is reported using a racemic gamma-alkoxy allyltitanate (17) and an optically active aldehyde (16) to deliver in good yield the anti adduct 18 as the major isomer. When the corresponding delta-lactol 24 was used in place of aldehyde 16, the anti adduct 25 was obtained in 94% yield as the only product. Structural modifications effected on 25 delivered aldehyde 28 which was in turn submitted to a second allylation reaction in the presence of the optically active titanated crotyl carbamate 2, prepared as described by Hoppe from crotyl carbamate 1, to conduct to compound 29 in 80% yield. This derivative corresponds to a potential precursor of the C1-C9 portion of Tylonolide, aglycon of Tylosin (4).

  DOI：

  10.1021/jo9807722