avermectin B_1a

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: avermectin B_1a
• 英文别名: 5-O-tert-butyldimethylsilylavermectin B1a；(1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-butan-2-yl-21'-[tert-butyl(dimethyl)silyl]oxy-24'-hydroxy-12'-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one
• 化学式: C₅₄H₈₆O₁₄Si
• 分子量: 987.354
• InChiKey: RZBWJGXCYYMHAL-LVBFSCRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.41
• 重原子数：
  69
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  avermectin B_1a 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-12'-[(2R,4S,5S,6S)-5-[(2S,4S,5R,6S)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-2-butan-2-yl-21'-[tert-butyl(dimethyl)silyl]oxy-24'-hydroxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one
  参考文献：
  名称：

  CN103613625

  摘要：

  公开号：
• 作为产物：
  描述：

  avermectin B_1a 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到avermectin B_1a
  参考文献：
  名称：

  Synthesis of 4″-alkoxy avermectin derivatives using rhodium carbenoid-mediated O–H insertion reaction

  摘要：

  4"-Alkoxy avermectin derivatives have been synthesized using O-H insertion reaction with ethyl diazoacetate in the presence of Rh-2(OAc)(4) as a catalyst. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.02.007

文献信息

• [EN] AVERMECTINS AND AVERMECTIN MONOSACCHARIDES SUBSTITUTED IN THE 4'- AND 4''-POSITION HAVING PESTICIDAL PROPERTIES<br/>[FR] AVERMECTINES ET MONOSACCHARIDES D'AVERMECTINE SUBSTITUES EN POSITION 4' ET 4'' A PROPRIETES PESTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2004069853A1

  公开（公告）日：2004-08-19

  What is described are a compound of the formula (I) wherein the bond of atoms C22 and C23 is a single or double bond; m is 0 or l; n is 0, 1 or 2; p is 0 or l; R1 is C1-C12-alkyl, C3-C8-cycloalkyl or C2-C12-alkenyl; R2 is for example H, C1-C12-alkyl, C1-C12-haloalkyl or C1-C12-hydroxyalkyl; or together with R4 form with the carbon to which they are bound for example a three- to seven-membered ring; R3 is for example H, C1-C12-alkyl, halogen, halo-C1-C2alkyl, CN, N02 or C3-C8cycloalkyl; R4 has the same meanings as R2; R5 and R6 independently of each other are for example H, C1-C12-alkyl, CN, N02, OH, SH, halogen, halo-C1-­C2alkyl or C3-C8cycloalkyl; or, if appropriate, an E/Z isomer, E/Z isomer mixture and/or tautomer thereof, in each case in free form or in salt form a process for preparing and using these compounds and their tautomers; pesticides whose active compound is selected from these compounds and their tautomers; and a process for preparing these compounds and compositions, and the use of these compounds and compositions.

  所描述的是一种式子为(I)的化合物，其中C22和C23原子的化学键为单键或双键；m为0或1；n为0、1或2；p为0或1；R1为C1-C12-烷基、C3-C8-环烷基或C2-C12-烯基；R2为例如H、C1-C12-烷基、C1-C12-卤代烷基或C1-C12-羟基烷基；或与R4一起形成与它们所连接的碳原子例如三至七元环；R3为例如H、C1-C12-烷基、卤素、卤代C1-C2-烷基、CN、N02或C3-C8-环烷基；R4具有与R2相同的含义；R5和R6彼此独立，例如H、C1-C12-烷基、CN、N02、OH、SH、卤素、卤代C1-C2-烷基或C3-C8-环烷基；或者，如果适用，是E/Z异构体、E/Z异构体混合物和/或其互变异构体，每种化合物均以自由形式或盐形式存在，以及制备和使用这些化合物及其互变异构体的方法；杀虫剂的活性化合物从这些化合物及其互变异构体中选择；以及制备这些化合物和组合物的方法，以及这些化合物和组合物的用途。
• Synthesis and biological activities of novel 4″-alkylidene avermectin derivatives
  作者：Kenichiro Nagai、Toshiaki Sunazuka、Kazuro Shiomi、Achim Harder、Andreas Turberg、Satoshi Ōmura

  DOI：10.1016/j.bmcl.2003.09.003

  日期：2003.11

  Horner-Emmons reaction of 4"-dehydro-5-O-TBDMS-avermectin B-1a with a variety of phosphorus ylides using LHMDS gave novel 4"-alkylidene avermectin derivatives in high yields. Further modifications led to derivatives bearing diverse functional groups. The new avermectin derivatives showed potent growth inhibitory activity against Artemia salina and Caenorhabditis elegans. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of 4″-alkoxy avermectin derivatives using rhodium carbenoid-mediated O–H insertion reaction
  作者：Kenichiro Nagai、Toshiaki Sunazuka、Satoshi Ōmura

  DOI：10.1016/j.tetlet.2004.02.007

  日期：2004.3

  4"-Alkoxy avermectin derivatives have been synthesized using O-H insertion reaction with ethyl diazoacetate in the presence of Rh-2(OAc)(4) as a catalyst. Published by Elsevier Ltd.
• CN103613625
  申请人：——

  公开号：——

  公开（公告）日：——