(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 | 1059187-48-2

• 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''S)-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,3S)-2-methyl-3-(oxan-2-yloxy)butyl]-1,3-dithian-2-yl]pentan-2-yl]oxy-dimethylsilane
• CAS: 1059187-48-2
• 化学式: C₃₁H₆₄O₄S₂Si₂
• 分子量: 621.15
• InChiKey: BFULNFSLBHGIBQ-NFMUTONDSA-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''S)-2-[4',5'-bis((tert-butyldimethylsilyl)oxy)-pentyl]-2-[2''-methyl-3''-((tetrahydropyran-2'''-yl)oxy)butyl]-1,3-dithiane 在 镍 氢气 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以89%的产率得到tert-butyl-[(2S,8R,9S)-1-[tert-butyl(dimethyl)silyl]oxy-8-methyl-9-(oxan-2-yloxy)decan-2-yl]oxy-dimethylsilane
  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：

  (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

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.