(2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester | 1192146-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester
• 英文别名: 5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester；methyl (2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-(2-oxoethyl)-5-phenylmethoxypentanoate
• CAS: 1192146-52-3
• 化学式: C₂₁H₃₄O₅Si
• 分子量: 394.583
• InChiKey: OJBHQYIGEOAHMU-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 palladium 10% on activated carbon 、 氢气 、 4-甲基苯磺酸吡啶 、 三苯基膦 、 pyridinium chlorochromate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 methyl (2R,3R)-2-(14-bromotetradecyl)-3-(tert-butyldimethylsilyloxy)hen-eicosanoate
  参考文献：
  名称：

  Thiol modified mycolic acids

  摘要：

  Patient serum antibodies to mycolic acids have the potential to be surrogate markers of active tuberculosis (TB) when they can be distinguished from the ubiquitously present cross-reactive antibodies to cholesterol. Mycolic acids are known to interact more strongly with antibodies present in the serum of patients with active TB than in patients with latent TB or no TB. Examples of single stereoisomers of mycolic acids with chain lengths corresponding to major homologues of those present in Mycobacterium tuberculosis have now been synthesised with a sulfur substituent on the terminal position of the alpha-chain; initial studies have established that one of these binds to a gold electrode surface, offering the potential to develop second generation sensors for diagnostic patient antibody detection. (c) 2013 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2013.03.004
• 作为产物：
  描述：

  (R)-2-[(R)-3-benzyloxy-1-(tert-butyldimethylsilanyloxy)-propyl]pent-4-enoic acid methyl ester 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 以88%的产率得到(2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester
  参考文献：
  名称：

  The synthesis of single enantiomers of mycobacterial ketomycolic acids containing cis-cyclopropanes

  摘要：

  We report the syntheses of a single enantiomer of an unprotected ketomycolic acids containing a cis-cyclopropane and of related hydroxy-mycolic acids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.099

文献信息

• Method for determining the presence or absence of a biomarker
  申请人：Gwenin Christopher David

  公开号：US09945852B2

  公开（公告）日：2018-04-17

  A method of determining the presence or absence in a sample of a biomarker, the method comprising: (a) linking an antigen to colloidal gold to provide a gold-antigen species; (b) contacting the gold-antigen species with the sample; (c) adding a diagnosis agent to the sample; and (d) observing the color of the sample.

  一种确定样本中生物标记物存在或不存在的方法，该方法包括：(a) 将抗原与胶体金连接以提供金-抗原物种；(b) 将金-抗原物种与样本接触；(c) 向样本中添加诊断剂；和 (d) 观察样本的颜色。
• Compounds for Use in Therapy
  申请人：Baird Mark Stephen

  公开号：US20110150981A1

  公开（公告）日：2011-06-23

  A compound of formula (I) for use in the treatment of a disease of the immune system; wherein R is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 50 carbon atoms; R 1 is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 40 carbon atoms; each of R 2 , Wand R 4 is independently selected from an optionally-substituted alkylene, alkenylene, alkynylene, arylene, arylalkylene or alkylarylene moiety having from 1 to 40 carbon atoms; each of X, Y and Z is independently selected from an optionally-substituted alkylene, alkenylene, alkenylene, arylene, alkylarylene, cycloalkylene, ketone, ester, amide, imide, imine, thioether, ether, thioester and thioketone; and P is selected from hydrogen, an alkyl group, a sugar residue, or a metal, phosphonium or ammonium species; wherein at least one of X, Y and Z includes a moiety selected from cyclopropyl, C=A, C-AH and C-OR 5 ; wherein R 5 is alkyl or haloalkyl, and A is O, S or Me, wherein R 6 may be H or 20 alkyl.

  化合物式（I）的化合物用于治疗免疫系统疾病；其中R是具有1至50个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；R1是具有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；R2，W和R4中的每一个都独立地选择自具有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团的取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；X，Y和Z中的每一个都独立地选择自可选取代的烷基，烯基，烯基，芳基，烷基芳基，环烷基，酮，酯，酰胺，亚酰胺，亚胺，硫醚，醚，硫酯和硫酮的基团；P从氢，烷基，糖残基或金属，膦，铵或铵物种中选择；其中X，Y和Z中至少有一个包括从环丙基，C = A，C-AH和C-OR5中选择的基团；其中R5是烷基或卤代烷基，A是O，S或Me，R6可能是H或20烷基。
• Adjuvants for Use in Vaccination
  申请人：Baird Mark Stephen

  公开号：US20110142916A1

  公开（公告）日：2011-06-16

  A compound of formula (I) for use as an adjuvant in vaccination; wherein R is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 50 carbon atoms; R 1 is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 40 carbon atoms; each of R 2 , R 3 and R 4 is independently selected from an optionally-substituted alkylene, alkenylene, alkynylene, arylene, arylalkylene or alkylarylene moiety having from 1 to 40 carbon atoms; each of X, Y and Z is independently selected from an optionally-substituted alkylene, alkenylene, alkynylene, arylene, alkylarylene or cycloalkylene, ketone, ester, amide, imide, imine, thioether, ether, thioester, thioketone; and P is selected from hydrogen, an alkyl group, a sugar residue, or a metal, phosphonium or ammonium species; wherein at least one of X, Y and Z includes a moiety selected from cyclopropyl, C=A, C-AH and C—OR 5 ; wherein R 5 is alkyl or haloalkyl, and A is S, O or NR 6 , wherein R 6 maybe H or 20 alkyl.

  化合物式（I）的复合物用作疫苗佐剂；其中R是具有1至50个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团; R1是具有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团; R2，R3和R4中的每一个都是独立选择的，具有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团; X，Y和Z中的每一个都是独立选择的，具有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，烷基芳基或环烷基，酮，酯，酰胺，亚酰胺，亚胺，硫醚，醚，硫酯，硫酮; P是氢，烷基，糖残基或金属，膦或铵物种中的一种；其中X，Y和Z中至少一个包括从环丙基，C=A，C-AH和C—OR5中选择的基团; 其中R5是烷基或卤代烷基，A是S，O或NR6，其中R6可以是H或20烷基。
• Compounds for use in therapy
  申请人：Baird Mark Stephen

  公开号：US08889894B2

  公开（公告）日：2014-11-18

  A compound of formula (I) for use in the treatment of a disease of the immune system; wherein R is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 50 carbon atoms; R1 is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 40 carbon atoms; each of R2, R3 and R4 is independently selected from an optionally-substituted alkylene, alkenylene, alkynylene, arylene, arylalkylene or alkylarylene moiety having from 1 to 40 carbon atoms; each of X, Y and Z is independently selected from an optionally-substituted alkylene, alkenylene, alkenylene, arylene, alkylarylene, cycloalkylene, ketone, ester, amide, imide, imine, thioether, ether, thioester and thioketone; and P is selected from hydrogen, an alkyl group, a sugar residue, or a metal, phosphonium or ammonium species; wherein at least one of X, Y and Z includes a moiety selected from cyclopropyl, C=A, C-AH and C—OR5; wherein R5 is alkyl or haloalkyl, and A is O, S or NR6, wherein R6 may be H or 20 alkyl.

  一种化合物的化学式（I），用于治疗免疫系统疾病；其中R是具有1-50个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；R1是具有1-40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；R2，R3和R4中的每一个都是独立选择的，选自具有1-40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；X，Y和Z中的每一个都是独立选择的，选自具有1-40个碳原子的可选取代的烷基，烯基，炔基，芳基，烷基芳基，环烷基，酮，酯，酰胺，亚酰胺，亚胺，硫醚，醚，硫代酯和硫代酮；P选自氢，烷基，糖残基或金属，膦或铵物种；其中X，Y和Z中至少一个包括从环丙基，C = A，C-AH和C-OR5中选择的基团；其中R5是烷基或卤代烷基，A是O，S或NR6，其中R6可以是H或20烷基。
• Adjuvants for use in vaccination
  申请人：Baird Mark Stephen

  公开号：US08728515B2

  公开（公告）日：2014-05-20

  A compound of formula (I) for use as an adjuvant in vaccination; wherein R is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 50 carbon atoms; R1 is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 40 carbon atoms; each of R2, R3 and R4 is independently selected from an optionally-substituted alkylene, alkenylene, alkynylene, arylene, arylalkylene or alkylarylene moiety having from 1 to 40 carbon atoms; each of X, Y and Z is independently selected from an optionally-substituted alkylene, alkenylene, alkynylene, arylene, alkylarylene or cycloalkylene, ketone, ester, amide, imide, imine, thioether, ether, thioester, thioketone; and P is selected from hydrogen, an alkyl group, a sugar residue, or a metal, phosphonium or ammonium species; wherein at least one of X, Y and Z includes a moiety selected from cyclopropyl, C=A, C-AH and C—OR5; wherein R5 is alkyl or haloalkyl, and A is S, O or NR6, wherein R6 maybe H or 20 alkyl.

  式(I)的化合物作为疫苗佐剂使用；其中R是含有1至50个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；R1是含有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；R2，R3和R4中的每一个都独立地选择自1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团的取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；X，Y和Z中的每一个都独立地选择自1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，烷基芳基或环烷基，酮，酯，酰胺，咪唑，亚胺，硫醚，醚，硫酯，硫酮；P选择自氢，烷基，糖残基或金属，膦或铵物种；其中X，Y和Z中至少一个包括从环丙基，C=A，C-AH和C—OR5中选择的基团；其中R5是烷基或卤代烷基，A是S，O或NR6，其中R6可以是H或20烷基。