(2'R,3'S)-2-[2'-methyl-3'-((tetrahydropyran-2''-yl)oxy)butyl]-1,3-dithiane | 1059187-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: (2'R,3'S)-2-[2'-methyl-3'-((tetrahydropyran-2''-yl)oxy)butyl]-1,3-dithiane
• 英文别名: 2-[(2S,3R)-4-(1,3-dithian-2-yl)-3-methylbutan-2-yl]oxyoxane
• CAS: 1059187-47-1
• 化学式: C₁₄H₂₆O₂S₂
• 分子量: 290.491
• InChiKey: QYJPKTDJMWMFGQ-OJRHAOMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2'R,3'S)-2-[2'-methyl-3'-((tetrahydropyran-2''-yl)oxy)butyl]-1,3-dithiane 、 pent-4-en-1-yl 4-methoxybenzoate 以152.0 mg的产率得到(4'S,2''R,3''S)-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 (4S,10R)-4-hydroxy-10-methyl-11-oxododec-2-en-1,4-olide and related bioactive marine butenolides

  摘要：

  Marine-derived microorganisms produce structurally diverse butenolides possessing a variety of bioactivities. Described here is the total synthesis of (4S, 10R)-4-hydroxy-10-nnethyl-11-oxododec-2-en-1,4-olide and a related butenolide containing anti stereochemistry at C10-C11. A three-module coupling strategy has been established for synthesis of the stereoisomers of the naturally Occurring butenolides by assembling the C3-C7 and C9-C12 fragments via double alkylation of a 1,3-dithiane. The C10-C11 stereochemistry could be easily controlled by an asymmetric aldol condensation, while the butenolide unit was efficiently constructed according to the ring-closing metathesis protocol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.028
• 作为产物：
  描述：

  1,3-二噻烷 、 (2'S,3'S)-2-(1'-iodo-2'-methyl-3'-butyloxy)tetrahydropyran 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以86%的产率得到(2'R,3'S)-2-[2'-methyl-3'-((tetrahydropyran-2''-yl)oxy)butyl]-1,3-dithiane
  参考文献：
  名称：

  Total synthesis of (4S,10R)-4-hydroxy-10-methyl-11-oxododec-2-en-1,4-olide and related bioactive marine butenolides

  摘要：

  Marine-derived microorganisms produce structurally diverse butenolides possessing a variety of bioactivities. Described here is the total synthesis of (4S, 10R)-4-hydroxy-10-nnethyl-11-oxododec-2-en-1,4-olide and a related butenolide containing anti stereochemistry at C10-C11. A three-module coupling strategy has been established for synthesis of the stereoisomers of the naturally Occurring butenolides by assembling the C3-C7 and C9-C12 fragments via double alkylation of a 1,3-dithiane. The C10-C11 stereochemistry could be easily controlled by an asymmetric aldol condensation, while the butenolide unit was efficiently constructed according to the ring-closing metathesis protocol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.028

文献信息

• Total synthesis of (4S,10R)-4-hydroxy-10-methyl-11-oxododec-2-en-1,4-olide and related bioactive marine butenolides
  作者：Wei-Min Dai、Lei Shi、Yannian Li

  DOI：10.1016/j.tetasy.2008.06.028

  日期：2008.7

  Marine-derived microorganisms produce structurally diverse butenolides possessing a variety of bioactivities. Described here is the total synthesis of (4S, 10R)-4-hydroxy-10-nnethyl-11-oxododec-2-en-1,4-olide and a related butenolide containing anti stereochemistry at C10-C11. A three-module coupling strategy has been established for synthesis of the stereoisomers of the naturally Occurring butenolides by assembling the C3-C7 and C9-C12 fragments via double alkylation of a 1,3-dithiane. The C10-C11 stereochemistry could be easily controlled by an asymmetric aldol condensation, while the butenolide unit was efficiently constructed according to the ring-closing metathesis protocol. (C) 2008 Elsevier Ltd. All rights reserved.