(2R,3R,4S,5S,6R)-(+)-6-(tert-butoxycarbonylamino)-3-[(tert-butyldimethylsilyl)oxy]-2,4-dimethyl-5-hydroxyheptanal N,O-acetonide | 368447-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2R,3R,4S,5S,6R)-(+)-6-(tert-butoxycarbonylamino)-3-[(tert-butyldimethylsilyl)oxy]-2,4-dimethyl-5-hydroxyheptanal N,O-acetonide
• 英文别名: tert-butyl (4R,5S)-5-[(2R,3S,4S)-3-[tert-butyl(dimethyl)silyl]oxy-4-methyl-5-oxopentan-2-yl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 368447-27-2
• 化学式: C₂₃H₄₅NO₅Si
• 分子量: 443.7
• InChiKey: VQUWPMPQYSIDPX-ZRSRNVLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6R)-(+)-6-(tert-butoxycarbonylamino)-3-[(tert-butyldimethylsilyl)oxy]-2,4-dimethyl-5-hydroxyheptanal N,O-acetonide 、 dimethyl diazomethylphosphonate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(2R,3S,4S,5R,6R)-(-)-2-(tert-butoxycarbonylamino)-5-[(tert-butyldimethylsilyl)oxy]-4,6-dimethyl-7-octyn-3-ol N,O-acetonide
  参考文献：
  名称：

  Synthesis of a C20−C26 Segment of Superstolide A by Addition of a Chiral Allenylzinc Reagent to (R)-N-Boc Alaninal

  摘要：

  Additions of chiral allenylzinc and indium reagents to N-Boc alaninal were examined as a possible route to a C20-C26 segment of superstolide A. Allenylzinc reagents, prepared in situ by palladiozincation of (R)- and (S)-5-pivalyloxy-3-butyn-2-ol mesylate, showed excellent reagent control to afford the anti,syn and anti,anti diastereomers as the nearly exclusive adducts.

  DOI：

  10.1021/ol050289v
• 作为产物：
  描述：

  (R)-2-(叔丁氧羰基氨基)丙醛 在 叔丁基过氧化氢 、 palladium diacetate 2,6-二甲基吡啶 、 titanium(IV) isopropylate 、 盐酸 、 L-(+)-酒石酸二乙酯 、 4 A molecular sieve 、 diethylzinc 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 三苯基膦 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 癸烷 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 100.0h， 生成 (2R,3R,4S,5S,6R)-(+)-6-(tert-butoxycarbonylamino)-3-[(tert-butyldimethylsilyl)oxy]-2,4-dimethyl-5-hydroxyheptanal N,O-acetonide
  参考文献：
  名称：

  Synthesis of a C20−C26 Segment of Superstolide A by Addition of a Chiral Allenylzinc Reagent to (R)-N-Boc Alaninal

  摘要：

  Additions of chiral allenylzinc and indium reagents to N-Boc alaninal were examined as a possible route to a C20-C26 segment of superstolide A. Allenylzinc reagents, prepared in situ by palladiozincation of (R)- and (S)-5-pivalyloxy-3-butyn-2-ol mesylate, showed excellent reagent control to afford the anti,syn and anti,anti diastereomers as the nearly exclusive adducts.

  DOI：

  10.1021/ol050289v

文献信息

• Yakelis, Neal A.; Roush, William R., Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 3838 - 3843
  作者：Yakelis, Neal A.、Roush, William R.

  DOI：——

  日期：——
• Studies towards the synthesis of superstolide A. Synthesis and stereochemical assignment of the C(21)C(26) fragment of superstolide A
  作者：Angela Zampella、Maria Valeria D'Auria

  DOI：10.1016/s0957-4166(01)00281-6

  日期：2001.7

  An asymmetric synthesis of the C(21) C(26) fragment of superstolide A is described. A fragment, corresponding to a reductive ozonolysis product of superstolide, as also prepared. Comparison of spectroscopic and optical properties of the corresponding fragment obtained by degraduation of natural superstolide A allowed the confirmation of the stereochemistry of the natural product. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of a C20−C26 Segment of Superstolide A by Addition of a Chiral Allenylzinc Reagent to (<i>R</i>)-<i>N</i>-Boc Alaninal
  作者：James A. Marshall、James J. Mulhearn

  DOI：10.1021/ol050289v

  日期：2005.4.14

  Additions of chiral allenylzinc and indium reagents to N-Boc alaninal were examined as a possible route to a C20-C26 segment of superstolide A. Allenylzinc reagents, prepared in situ by palladiozincation of (R)- and (S)-5-pivalyloxy-3-butyn-2-ol mesylate, showed excellent reagent control to afford the anti,syn and anti,anti diastereomers as the nearly exclusive adducts.