methyl (2R,3R,5S)-3-tert-butyldimethylsilyoxy-2-methyl-5-(2-trimethylsilylethoxy)methoxy-6-oxohexanoate | 332837-75-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2R,3R,5S)-3-tert-butyldimethylsilyoxy-2-methyl-5-(2-trimethylsilylethoxy)methoxy-6-oxohexanoate
• 英文别名: methyl (2R,3R,5S)-3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-6-oxo-5-(2-trimethylsilylethoxymethoxy)hexanoate
• CAS: 332837-75-9
• 化学式: C₂₀H₄₂O₆Si₂
• 分子量: 434.721
• InChiKey: RLIGRKWRHPMUJD-FGTMMUONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-1-(tert-Butyl-dimethyl-silanyl)-4-((E)-2-iodo-propenyl)-3-methyl-azetidin-2-one 、 methyl (2R,3R,5S)-3-tert-butyldimethylsilyoxy-2-methyl-5-(2-trimethylsilylethoxy)methoxy-6-oxohexanoate 、 [(E)-(S)-5-Benzenesulfonyl-4-methyl-1-((E)-2-tributylstannanyl-vinyl)-pent-3-enyloxy]-tert-butyl-dimethyl-silane 生成 (1S,2S,3R,4R,6S,12S,17R,7E,9E,13E,15E)-1,3,9,15-tetramethyl-6-(2-trimethylsilylethoxy)methoxy-19-oxo-18-azabicyclo[15.2.0]nonadeca-7,9,13,15-tetraene-2,4,12-triol
  参考文献：
  名称：

  An approach to the total synthesis of lankacidins: synthesis of advanced macrocyclic precursors

  摘要：

  The macrocyclic tetraenes 11 and 19, possible precursors of lankacidin C 1, have been prepared using intramolecular Stille reactions to close the macrocyclic rings. The Stille precursor 10 was prepared by stereoselective acylation of the azetidinone 3 using the thioester 7. After reduction and deprotection, cyclisation gave the macrocyclic product 11 in 55% yield. Alternatively, the Boc-protected amino-ester 17 was prepared by ring-opening of the azetidinone, and cyclised to the macrocycle 19 in 48% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02261-9
• 作为产物：
  描述：

  methyl (3R,5S)-6-(4,4'-dimethoxytriphenyl)methoxy-3-hydroxy-5-(2-trimethylsilylethoxy)methoxyhexanoate 在 2,6-二甲基吡啶 、 二氯乙酸 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 四甲基乙二胺 、 4 A molecular sieve 、 lithium diisopropyl amide 作用下， 反应 2.0h， 生成 methyl (2R,3R,5S)-3-tert-butyldimethylsilyoxy-2-methyl-5-(2-trimethylsilylethoxy)methoxy-6-oxohexanoate
  参考文献：
  名称：

  lankacidins的全合成的一种方法：必要的组成部分的合成

  摘要：

  概述了兰卡酸C 1的全合成策略，并合成了必要的结构单元。氮杂环丁酮4是由2-丁酸甲酯6通过以下途径制备的：其特征在于将三丁基锡铜酸盐立体选择性地添加至炔烃，不对称的醛醇缩合和通过分子内的Mitsunobu反应形成氮杂环丁酮。再次使用不对称醛醇缩合反应作为关键步骤，由苹果酸二甲酯18制得醛3，由丙-2-炔醇27制得砜3。

  DOI：

  10.1016/s0040-4039(00)02260-7

文献信息

• Synthesis of macrocyclic precursors of lankacidins using Stille reactions of 4-(2-iodo-alkenyl)azetidinones and related compounds for ring closure
  作者：Christopher T. Brain、Anqi Chen、Adam Nelson、Nongluk Tanikkul、Eric J. Thomas

  DOI：10.1016/j.tet.2010.04.129

  日期：2010.8

  In the context of a proposed total synthesis of lankacidins, the synthesis of 4-(2-iodo-alkenyl)azetidinones and their participation in Stille coupling reactions have been investigated. 1-tert-Butyldimethylsilyl-4-(2-iodoethenyl)azetidinone was found to undergo a Stille coupling reaction with a 3-hydroxy-1-tributylstannylhepta-1,5-diene to give an acceptable yield of the corresponding conjugated diene

  在拟议的lankacidins的全合成中，对4-（2-碘-烯基）氮杂环丁酮的合成及其在Stille偶联反应中的参与进行了研究。发现1-叔丁基二甲基甲硅烷基-4-（2-碘乙烯基）氮杂环丁酮与3-羟基-1-三丁基锡烷基庚基-1,5-二烯进行Stille偶联反应，得到可接受的相应共轭二烯收率，但类似与3-叔丁基二甲基甲硅烷氧基-1-三丁基锡烷基庚-1,5-二烯的反应不成功。还发现一系列4-[（（E）-2-碘丙-1-烯基]氮杂环丁酮，开环酯和内酯与3-三丁基锡烷基丙-2-烯醇进行Stille反应，尽管产率不同。甲基（2 R，3 R，5 S）-3-叔丁基二甲基甲硅烷氧基-2-甲基-5-（2-三甲基甲硅烷基乙氧基）甲氧基-6-氧己酸酯，（3 R，4 S）-1-叔丁基二甲基甲硅烷基-4-[[ E）-2-碘丙-1-基] -3-甲基氮杂环丁烷-2-one和（5 S，2 E，6 E）-5-叔然后研究了丁基丁基
• An approach to the total synthesis of lankacidins: synthesis of the requisite building blocks
  作者：Christopher T Brain、Anqi Chen、Adam Nelson、Nongluk Tanikkul、Eric J Thomas

  DOI：10.1016/s0040-4039(00)02260-7

  日期：2001.2

  A strategy for a total synthesis of lankacidin C 1 is outlined and the requisite building blocks synthesised. The azetidinone 4 was prepared from methyl but-2-ynoate 6 via a route which features the stereoselective addition of a tributyltin cuprate to the alkyne, an asymmetric aldol condensation and formation of the azetidinone by an intramolecular Mitsunobu reaction. The aldehyde 3 was prepared from

  概述了兰卡酸C 1的全合成策略，并合成了必要的结构单元。氮杂环丁酮4是由2-丁酸甲酯6通过以下途径制备的：其特征在于将三丁基锡铜酸盐立体选择性地添加至炔烃，不对称的醛醇缩合和通过分子内的Mitsunobu反应形成氮杂环丁酮。再次使用不对称醛醇缩合反应作为关键步骤，由苹果酸二甲酯18制得醛3，由丙-2-炔醇27制得砜3。
• An approach to the total synthesis of lankacidins: synthesis of advanced macrocyclic precursors
  作者：Anqi Chen、Adam Nelson、Nongluk Tanikkul、Eric J Thomas

  DOI：10.1016/s0040-4039(00)02261-9

  日期：2001.2

  The macrocyclic tetraenes 11 and 19, possible precursors of lankacidin C 1, have been prepared using intramolecular Stille reactions to close the macrocyclic rings. The Stille precursor 10 was prepared by stereoselective acylation of the azetidinone 3 using the thioester 7. After reduction and deprotection, cyclisation gave the macrocyclic product 11 in 55% yield. Alternatively, the Boc-protected amino-ester 17 was prepared by ring-opening of the azetidinone, and cyclised to the macrocycle 19 in 48% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.