(4'S,2''R,3''R)-2-[4',5'-bis((tert-butyldimethylsilyl)oxy)pentyl]-2-[2''-methyl-3''-((tetrahydropyran-2-yl)oxy)butyl]-1,3-dithiane | 1206551-63-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (4'S,2''R,3''R)-2-[4',5'-bis((tert-butyldimethylsilyl)oxy)pentyl]-2-[2''-methyl-3''-((tetrahydropyran-2-yl)oxy)butyl]-1,3-dithiane
• 英文别名: tert-butyl-[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-5-[2-[(2R,3R)-2-methyl-3-(oxan-2-yloxy)butyl]-1,3-dithian-2-yl]pentan-2-yl]oxy-dimethylsilane
• CAS: 1206551-63-4
• 化学式: C₃₁H₆₄O₄S₂Si₂
• 分子量: 621.15
• InChiKey: BFULNFSLBHGIBQ-WRENHGGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.09
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4'S,2''R,3''R)-2-[4',5'-bis((tert-butyldimethylsilyl)oxy)pentyl]-2-[2''-methyl-3''-((tetrahydropyran-2-yl)oxy)butyl]-1,3-dithiane 在 氢气 、 镍 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以93%的产率得到(2'S,8'R,9'R)-2-[1',2'-bis((tert-butyldimethylsilyl)oxy)-8'-methyl-9'-decyloxy]tetrahydropyran
  参考文献：
  名称：

  Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone

  摘要：

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.115
• 作为产物：
  描述：

  (S)-4,5-bis((tert-butyldimethylsilyl)oxy)-1-iodo-pentane 、 (2'R,3'R)-2-[2'-methyl-3'-((tetrahydropyran-2''-yl)oxy)butyl]-1,3-dithiane 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以85%的产率得到(4'S,2''R,3''R)-2-[4',5'-bis((tert-butyldimethylsilyl)oxy)pentyl]-2-[2''-methyl-3''-((tetrahydropyran-2-yl)oxy)butyl]-1,3-dithiane
  参考文献：
  名称：

  Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone

  摘要：

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.115

文献信息

• Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone
  作者：Yan Wang、Wei-Min Dai

  DOI：10.1016/j.tet.2009.10.115

  日期：2010.1

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.