farnesyl trichloroacetimidate | 852383-98-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: farnesyl trichloroacetimidate
• 英文别名: [(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] 2,2,2-trichloroethanimidate
• CAS: 852383-98-3
• 化学式: C₁₇H₂₆Cl₃NO
• 分子量: 366.759
• InChiKey: RSKGHYPRFHXITH-GRGUIBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  farnesyl trichloroacetimidate 在 sodium hydroxide 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Novel fluorescent analogues for transmembrane movement study of polyprenyl phosphates

  摘要：

  In order to investigate the transmembrane movement of polyprenyl phosphate across biological membranes, NBD (7-nitrobenz-2-oxa-1,3-diazol-4-yl)-labeled polyprenyl phosphate analogues were prepared. These analogues proved to be possible tools for a direct observation of the transmembrane flip-flop movement of polyprenyl phosphates by use of a sodium dithionitequenching procedure. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.049
• 作为产物：
  描述：

  反式,反式-金合欢醇 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以78%的产率得到farnesyl trichloroacetimidate
  参考文献：
  名称：

  Novel fluorescent analogues for transmembrane movement study of polyprenyl phosphates

  摘要：

  In order to investigate the transmembrane movement of polyprenyl phosphate across biological membranes, NBD (7-nitrobenz-2-oxa-1,3-diazol-4-yl)-labeled polyprenyl phosphate analogues were prepared. These analogues proved to be possible tools for a direct observation of the transmembrane flip-flop movement of polyprenyl phosphates by use of a sodium dithionitequenching procedure. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.049

文献信息

• Synthesis of putative chain terminators of mycobacterial arabinan biosynthesis
  作者：Iain A. Smellie、Sanjib Bhakta、Edith Sim、Antony J. Fairbanks

  DOI：10.1039/b704788f

  日期：——

  The synthesis of a variety of arabinose derivatives that have been modified at C-5 was achieved from D-arabinose. The 5-fluoro and 5-methoxy compounds were converted into the corresponding farnesyl phosphodiesters as putative chain terminators of mycobacterial arabinan biosynthesis. Biological testing of these materials revealed no effective anti-mycobacterial activity.

  以 D-阿拉伯糖为原料，合成了多种 C-5 修饰的阿拉伯糖衍生物。5 -氟和 5 -甲氧基化合物被转化为相应的法呢基磷酸二酯，作为霉菌阿拉伯糖生物合成的假定链终止器。对这些材料进行的生物测试表明，它们没有有效的抗霉菌活性。
• Synthesis of 2-deoxy-2-fluoro analogs of polyprenyl β-d-arabinofuranosyl phosphates
  作者：Maju Joe、Todd L. Lowary

  DOI：10.1016/j.carres.2006.08.020

  日期：2006.11

  Described is the synthesis of polyprenyl 2-deoxy-2-fluoro-beta-D-arabinofuranosyl phosphate derivatives, including an analog of decaprenyl P-D-arabinofuranosyl phosphate, the donor species used by the arabinosyltransferases involved in mycobacterial cell-wall biosynthesis. The targets were synthesized via a route involving the synthesis of a protected beta-D-arabinofuranosyl phosphate derivative, its coupling with a polyprenyl trichloroacetimidate, and then deprotection of the resulting product. The use of arabinofuranosyl phosphates with the monosaccharide hydroxyl groups protected as either silyl ethers or benzoate esters was explored. Although the coupling yields between the phosphate and polyprenyl trichloroacetimidates were comparable with either type of protecting group, access to the benzoyl-protected derivative was more efficient and therefore gave the products in higher overall yield. (c) 2006 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of farnesylphosphoryl β-d-arabinofuranose
  作者：Avraham Liav、Patrick J. Brennan

  DOI：10.1016/j.tetlet.2005.02.151

  日期：2005.4

  Decaprenylphosphoryl beta-D-arabinofuranose (DPA) is a key arabinose donor in mycobacteria. In an effort to establish a practical synthetic scheme for DPA, the synthesis of nerylphosphoryl and farnesylphosphoryl beta-D-arabinofuranoses has been developed. The products were obtained by coupling of a suitably protected P-D-arabinofuranosyl phosphate intermediate with activated forms of the C-10 nerol and C-15 trans,trans-farnesol and subsequent deprotection. (c) 2005 Elsevier Ltd. All rights reserved.