(3S,3S)-2-azido-3-tert-butoxycarbonylamino-1,4-butyrolactone | 104227-72-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,3S)-2-azido-3-tert-butoxycarbonylamino-1,4-butyrolactone
• 英文别名: (2S,3S)-2-azido-3-(tert-butoxycarbonylamino)-4-butanolide；(3S,4S)-4-azido-5-oxotetrahydro-3-furanylcarbamic acid tert-butyl ester；tert-butyl (3S,4S)-4-azido-5-oxotetrahydro-3-furanylcarbamate；tert-butyl N-[(3S,4S)-4-azido-5-oxooxolan-3-yl]carbamate
• CAS: 104227-72-7
• 化学式: C₉H₁₄N₄O₄
• 分子量: 242.235
• InChiKey: ZTHRPSKRSGFNII-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,3S)-2-azido-3-tert-butoxycarbonylamino-1,4-butyrolactone 生成 (2S,3S)-3-amino-2-azido-4-hydroxybutanoic acid
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-3-叔丁氧羰基氨基-gamma-丁酸内酯 在 对甲苯磺酰叠氮 、 lithium hexamethyldisilazane 作用下， 生成 (3S,3S)-2-azido-3-tert-butoxycarbonylamino-1,4-butyrolactone
  参考文献：
  名称：

  使用离子和自由基反应高度立体控制合成 2,3-二取代 1,4-丁内酯

  摘要：

  N-取代的 3-氨基-1,4-丁内酯通过阴离子和自由基过程进行高度立体控制的取代反应。

  DOI：

  10.1139/v93-182

文献信息

• Diamine derivatives
  申请人：Ohta Toshiharu

  公开号：US20050020645A1

  公开（公告）日：2005-01-27

  A compound represented by the general formula (1): Q 1 -Q 2 -T 0 -N(R 1 )-Q 3 -N(R 2 )-T 1 -Q 4 (1) wherein R 1 and R 2 are hydrogen atoms or the like; Q 1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q 2 is a single bond or the like; Q 3 is a group in which Q 5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T 0 and T 1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

  通用式（1）表示的化合物： Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4（1） 其中R1和R2是氢原子或类似物；Q1是饱和或不饱和的、5-或6-成员环烃基，可以被取代，或类似物；Q2是单键或类似物；Q3是一个基团，其中Q5是具有1至8个碳原子的烷基基团，或类似物；T0和T1是羰基团或类似物；其盐、溶剂合物或N-氧化物。 该化合物可用作预防和/或治疗脑梗死、脑栓塞、心肌梗死、心绞痛、肺梗死、肺栓塞、布尔格病、深静脉血栓形成、弥散性血管内凝血综合征、瓣膜或关节置换后的血栓形成、血管成形术后的血栓形成和再闭塞、全身性炎症反应综合征（SIRS）、多器官功能障碍综合征（MODS）、体外循环期间的血栓形成，或抽血时的血液凝结。
• Enantioselective synthesis of 2-isocephem and 2-isooxacephem antibiotics
  作者：Hajime Nitta、Ikuo Ueda、Minoru Hatanaka

  DOI：10.1039/a700650k

  日期：——

  The azido lactone 8 was prepared in a highly stereoselective manner by introduction of an azide function to the lactone 6 derived from L-aspartic acid, and then was converted into (2S,3S)-3-amino-2-azido-4-hydroxybutanoic acid 4. Four-component condensation of the amino acid 4, p-nitrobenzyl isocyanide and formaldehyde or 2,2-diethoxyacetaldehyde furnished the corresponding 3,4-cis-azetidinone 16 or 26 in excellent yield. 3-Methoxy-2-isooxacephalosporin was prepared by the intramolecular acylation of imidazolide 23 derived from compound 16. 3-Unsubstituted 2-isocephem and 2-isooxacephem analogues were prepared from the azetidinone 26.

  叠氮内酯 8 是以高度立体选择性的方式制备的，方法是在 L-天冬氨酸衍生的内酯 6 中引入叠氮功能，然后将其转化为 (2S,3S)-3-氨基-2-叠氮-4-羟基丁酸 4。 将氨基酸 4、对硝基苄基异氰酸酯和甲醛或 2,2-二乙氧基乙醛进行四组份缩合，可得到相应的 3,4-顺式氮杂环丁酮 16 或 26，收率极高。从氮杂环丁酮 26 中制备出了 3-未取代的 2-异头孢和 2-异头孢类似物。
• Highly stereocontrolled syntheses of 2,3-disubstituted 1,4-butyrolactones using ionic and free radical reactions
  作者：Stephen Hanessian、Benoit Vanasse、Hua Yang、Marco Alpegiani

  DOI：10.1139/v93-182

  日期：1993.9.1

  N-Substituted 3-amino-1,4-butyrolactones undergo highly stereocontrolled substitution reactions via anionic and free radical processes.

  N-取代的 3-氨基-1,4-丁内酯通过阴离子和自由基过程进行高度立体控制的取代反应。
• An enantioselective synthesis of 2-isocephem and 2-iso-oxacephem nuclei
  作者：Hajime Nitta、Minoru Hatanaka、Toshiyasu Ishimaru

  DOI：10.1039/c39870000051

  日期：——

  A stereocontrolled synthesis of optically active 2-isocephem and 2-iso-oxacephem nuclei is described starting from L-aspartic acid.

  从L-天冬氨酸开始描述了光学活性的2-异欧芬和2-异-氧杂蒽芬核的立体控制合成。
• Diamine Derivatives
  申请人：Ohta Toshiharu

  公开号：US20110312990A1

  公开（公告）日：2011-12-22

  A compound represented by the general formula (1): -Q 1 -Q 2 -T 0 -N(R 1 )-Q 3 -N(R 2 )-T 1 -Q 4 (1) wherein R 1 and R 2 are hydrogen atoms or the like; Q 1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q 2 is a single bond or the like; Q 3 is a group in which Q 5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T 0 and T 1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

  化合物的一般式表示为(1)：-Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4(1)，其中R1和R2为氢原子或类似物；Q1为饱和或不饱和的5-或6-成员环烃基，可以是取代基或类似物；Q2为单键或类似物；Q3为其中Q5为1至8个碳原子的烷基或类似物的基团；T0和T1为羰基或类似物。该化合物及其盐、溶剂化物或N-氧化物可用于预防和/或治疗脑梗死、脑栓塞、心肌梗死、心绞痛、肺梗死、肺栓塞、布尔格病、深静脉血栓形成、弥散性血管内凝血综合征、瓣膜或关节置换后的血栓形成、血管成形术后的血栓形成和再闭塞、全身性炎症反应综合征(SIRS)、多器官功能障碍综合征(MODS)、体外循环期间的血栓形成或采血时的血液凝固。