多西他赛杂质9 | 161759-90-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 多西他赛杂质9
• 英文名称: (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate
• 英文别名: (2S,3R)-methyl 2-hydroxy-3-(N-tert-butoxycarbonyl)amino-3-phenylpropionate；methyl (2S,3R)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropanoate；methyl (3R)-tert-butoxycarbonylamino-(2S)-hydroxy-3-phenylpropionate；(2S,3R)-Methyl 3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoate；methyl (2S,3R)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
• CAS: 161759-90-6
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: NCALQERIBRYGOK-NEPJUHHUSA-N

物化性质

• 熔点：
  131-132 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  443.3±45.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  多西他赛杂质9 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以69.4%的产率得到(2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol
  参考文献：
  名称：

  Determination of the Structure and Its Absolute Configuration of 2”-Hydroxynicotianamine, an Inhibitor against Angiotensin-I Converting Enzyme in Buckwheat, through the Total Synthesis

  摘要：

  Nicotianamine is known as an inhibitor against Angiotensin-1 Converting Enzyme (ACE). We synthesized a new nicotianamine derivative with an additional hydroxy group isolated from buckwheat (Fagopyrum esculentutn Moench) powder and determined its regio and stereochemistry unambiguously by the enantioselective synthesis of diastereomers.

  DOI：

  10.3987/com-10-11931
• 作为产物：
  描述：

  (2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol 在 咪唑 、 4-二甲氨基吡啶 、 ruthenium(IV) oxide 、 sodium periodate 、 左旋樟脑磺酸 、 四丁基氟化铵 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 17.5h， 生成 多西他赛杂质9
  参考文献：
  名称：

  Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine

  摘要：

  A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and alpha-hydroxy-beta-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00741-8

文献信息

• A novel method to synthesize docetaxel and its isomer with high yields
  作者：Chuan-Min Qi、Yun-Feng Wang、Ling-Chun Yang

  DOI：10.1002/jhet.5570420430

  日期：2005.5

  Single crystal of (3S,4R)-3-hydroxy-N-[(S)-(l-phenyl)ethyl]-4 -(2′-chlorophenyl) -2-azetidinone (4c) was obtained, the configuration of which was determined by X-ray diffraction. Because of the mild cyclization reaction condition and convenient asymmetric resolution operation when p-chlorobenzaldehyde was employed instead of benzaldehyde, the yield of cyclization and hydrogenation increased dramatically

  多西他赛及其异构体的侧链是通过施陶丁格环加成反应和以氯苯甲醛为起始原料对氯苯基中间体进行催化加氢而获得的。描述了通过不同取代位置的氯苯基手性胺席夫碱的斯托丁格环加成反应合成三种新型手性氮杂环丁酮衍生物，并在Pd / MgCO 3或Pd / C催化下开环反应得到多西他赛的侧链研究了其高产异构体。最后，获得多西他赛及其异构体。（3 S，4 R）-3-羟基-N -[（S）-（1-苯基）乙基] -4-（2'-氯苯基）-2-氮杂环丁酮的单晶（4c得到），通过X射线衍射确定其构型。由于使用温和的环化反应条件和方便的不对称拆分操作，当使用对氯苯甲醛代替苯甲醛时，环化和氢化的收率急剧增加，多西他赛的总收率高于文献中的结果。当使用邻氯苯甲醛代替苯甲醛时，通过相同的方法获得了多西他赛的异构体。
• [EN] IMPROVED AMINOHYDROXYLATION OF ALKENES<br/>[FR] AMINOHYDROXYLATION AMÉLIORÉE D'ALCÈNES
  申请人：IND RES LTD

  公开号：WO2011159177A1

  公开（公告）日：2011-12-22

  The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

  该发明涉及一种使用N-氧羰酸酯试剂（例如N-酰氧羰酸酯、N-烷氧羰酸酯和N-芳基氧羰酸酯试剂）对烯烃进行氨羟基化的方法。该发明特别涉及一种可以在无需添加碱的情况下进行的分子间氨羟基化反应。该发明还涉及新颖的N-氧羰酸酯试剂，这些试剂是稳定的结晶材料。该发明的方法在合成具有邻位氨基醇基团的化合物方面非常有用，例如具有生物活性的化合物。
• Synthesis of (−)-bestatin and the Taxotere® side-chain via nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate
  作者：Iwona Kudyba、Jerzy Raczko、Janusz Jurczak

  DOI：10.1016/j.tetlet.2003.09.154

  日期：2003.11

  The nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate 6 with 1-nitro-2-phenylethane or with phenylnitromethane led stereoselectively to adducts 4 and 12, which where then transformed into (−)-bestatin hydrochloride and the Taxotere® side-chain in overall yields of 31 and 52%.

  （1 R）-8-苯基薄荷基乙醛酸酯6与1-硝基-2-苯基乙烷或苯基硝基甲烷的硝基醛反应立体选择性地导致加合物4和12，然后将其转化为（-）-贝他汀盐酸盐和Taxotere®侧-链的总收益率分别为31％和52％。
• Asymmetric Nitroaldol Reaction. Synthesis of Taxotere Side Chain and (−)-Bestatin Using (1<i>R</i>)-8-Phenylmenthyl Glyoxylate
  作者：Iwona Kudyba、Jerzy Raczko、Janusz Jurczak

  DOI：10.1021/jo0358269

  日期：2004.4.1

  (1R)-8-phenylmenthyl glyoxylate (3b) with 1-nitro-1-phenylmethane (4) or with 1-nitro-2-phenylethane (13) led stereoselectively to adducts syn-2b and syn-12b, which were then transformed into the Taxotere side chain and (−)-bestatin hydrochloride in overall yields of 52% and 31%, respectively.

  （1所述的硝基醛醇反应- [R）-8-苯基薄荷基乙醛酸（图3b）与1-硝基-1-苯基甲烷（4），或与1-硝基-2-苯基乙烷（13立体选择性地导致加合物）顺式-图2b和顺式12b的，然后分别转化为Taxotere侧链和（-）-bestatin盐酸盐，总收率分别为52％和31％。
• AMINOHYDROXYLATION OF ALKENES
  申请人：Mee Simon Peter Harold

  公开号：US20130274479A1

  公开（公告）日：2013-10-17

  The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

  本发明涉及使用N-氧化氨基甲酸酯试剂（例如N-酰氧基氨基甲酸酯、N-烷氧羰氧甲酸酯和N-芳烃氧羰氧甲酸酯试剂）进行烯烃氨基羟化的方法。本发明特别涉及可以在无添加碱的情况下进行的分子间氨基羟化反应。本发明还涉及新颖的N-氧化氨基甲酸酯试剂，其为稳定的晶体材料。本发明的方法在合成具有邻位氨基醇基团的化合物（例如具有生物活性的化合物）方面非常有用。