Boc-D-丝氨酸苄酯 | 59524-02-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丝氨酸类衍生物
• 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
• 中文名称: Boc-D-丝氨酸苄酯
• 中文别名: BOC-D-丝氨酸苄酯
• 英文名称: (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate
• 英文别名: Boc-D-Ser-OBn；N-Boc-D-Serine benzyl ester；Boc-(D)-serine benzyl ester；N-tBOC-O-benzyl-D-serine；N-Boc-O-benzyl-D-serine；Benzyl 2(R)-[(tert-butoxycarbonyl)amino]-3-hydroxypropionate；Boc-D-Ser-OBzl；benzyl (2R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 59524-02-6；145612-59-5；141527-78-8
• 化学式: C₁₅H₂₁NO₅
• mdl: MFCD00080265
• 分子量: 295.335
• InChiKey: BQADRZHPZVQGCW-GFCCVEGCSA-N

物化性质

• 熔点：
  66-70℃
• 沸点：
  458.8±40.0 °C(Predicted)
• 密度：
  1.174

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.466
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  Boc-D-丝氨酸苄酯 在 吡啶 、 sodium periodate 、 氯化亚砜 、 ruthenium(III) trichloride hydrate 、 palladium 10% on activated carbon 、 氢气 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， -42.0~20.0 ℃ 、482.64 kPa 条件下， 反应 15.75h， 生成 (4R)-3-(tert-butyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Stereoselective synthesis of lanthionine derivatives in aqueous solution and their incorporation into the peptidoglycan of Escherichia coli

  摘要：

  The three diastereoisomers-(R,R), (S,S) and meso-of lanthionine were synthesized in aqueous solution with high diastereoselectivity (>99%). The (S) and (R) enantiomers of two differently protected sulfamidates were opened by nucleophilic attack of (R) or (S)-cysteine. Acidification and controlled heating liberated the free lanthionines. Using the same chemistry, an α-benzyl lanthionine was also prepared. The proposed method, which avoids the need of enrichment by recrystallization, opens the way to the labelling of these compounds with (35)S. Furthermore, in vivo bioincorporation into Escherichia coli W7 was studied. No incorporation of α-benzyl lanthionine was observed. In contrast, meso-lanthionine can effectively replace meso-diaminopimelic acid in vivo, while in the presence of (R,R)-lanthionine the initial increase of bacterial growth was followed by cell lysis. In the future, meso-[(35)S]lanthionine could be used to study the biosynthesis of peptidoglycan and its turnover in relation to cell growth and division.

  DOI：

  10.1016/j.bmc.2014.07.023
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium hydride 、 碳酸氢钠 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 Boc-D-丝氨酸苄酯
  参考文献：
  名称：

  基于螺吲哚啉的生长激素促分泌素MK-677的简便合成

  摘要：

  摘要描述了一种合成基于口服活性螺环二氢吲哚的生长激素促分泌素MK-677的简便方法。关键步骤采用了菲舍尔吲哚/还原策略。还优化了关键中间体N-保护的哌啶羧醛5和N-Boc-O-苄基-d-丝氨酸（2）的制备。

  DOI：

  10.1016/j.cclet.2012.03.032

文献信息

• A Practical Aryl Unit for Azlactone Dynamic Kinetic Resolution: Orthogonally Protected Products and A Ligation-Inspired Coupling Process
  作者：Sean Tallon、Francesco Manoni、Stephen J. Connon

  DOI：10.1002/anie.201406857

  日期：2015.1.12

  The first strategy for bringing about enantioselective azlactone dynamic kinetic resolution to generate orthogonally protected amino acids has been developed. In the presence of a C2‐symmetric squaramide‐based catalyst, benzyl alcohol reacts with novel yet readily prepared tetrachloroisopropoxycarbonyl‐substituted azlactones to generate trapped phthalimide products of significant synthetic interest

  已经开发出用于产生对映选择性氮杂内酯动态动力学拆分以产生正交保护的氨基酸的第一种策略。在C的存在下2 -对称的基于方酰胺的催化剂，苯甲醇与新型的但易于制备的四氯异丙氧基羰基取代的内酯反应，生成具有重要对映体控制意义的，具有重大合成意义的被困邻苯二甲酰亚胺产品。这些材料是被掩盖的氨基酸，它们被证明是正交保护的：邻苯二甲酰亚胺的裂解可以在酯的存在下实现，反之亦然。该过程可用于使受保护的丝氨酸（以化学计量负载）与衍生自天然和非生物氨基酸的外消旋a内酯进行高度立体选择性的连接型偶联。脱保护后，随后的碱基介导的O→N酰基转移发生，形成二肽。
• Synthesis of Sialyl Lewis X Mimetics and Related Structures Using the Glycosyl Phosphite Methodology and Evaluation of E-Selectin Inhibition
  作者：Chun-Cheng Lin、Makoto Shimazaki、Marie-Pierre Heck、Shin Aoki、Ruo Wang、Teiji Kimura、Helena Ritzèn、Shuichi Takayama、Shih-Hsiung Wu、Gabriel Weitz-Schmidt、Chi-Huey Wong

  DOI：10.1021/ja952265x

  日期：1996.1.1

  reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis X (Lex), Lewis Y (Ley), glycopeptides, and sialyl Lewis X (SLex) mimetics. Both α-O-fucosyl-l-threonine and α-O-fucosyl-(1R,2R)-2-aminocyclohexanol were found to be effective templates for the chemical/enzymatic synthesis of SLex mimetics, and some fucopeptides prepared were 5−10 times more active than SLex as

  本文描述了我们最近对用于糖基化反应的糖基亚磷酸酯的研究，特别强调了保护基团和立体化学对异头反应性和立体选择性的影响的研究，以及该方法在合成 Lewis X (Lex)、Lewis Y 中的应用(Ley)、糖肽和唾液酸路易斯 X (SLex) 模拟物。发现 α-O-岩藻糖基-l-苏氨酸和 α-O-岩藻糖基-(1R,2R)-2-氨基环己醇都是 SLex 模拟物化学/酶促合成的有效模板，制备的一些岩藻肽是 5-10作为 E-选择素抑制剂的活性比 SLex 高出数倍。
• Efficient asymmetric synthesis of N-protected-β-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid
  作者：Rajesh Malhotra、Tushar K. Dey、Swarup Dutta、Sourav Basu、Saumen Hajra

  DOI：10.1039/c4ob01047g

  日期：——

  First regioselective ring opening of serine derived cyclic sulfamidate by hard nucleophiles like ArONa is developed, where β-elimination of serine sulfamidate ester by stronger nucleophiles is overcome by reversal of the electronic effect of the carboxylate anion. This method provides easy and direct access to a variety of N-Boc- and N-PMB protected β-aryloxy-α-amino acids with complete retention of enantiopurity in moderate to high yields.

  发展了一种首个区域选择性的丝氨酸衍生环状硫酰胺在强亲核试剂（如ArONa）作用下开环的方法，其中通过羧酸根阴离子的电子效应反转克服了强亲核试剂对丝氨酸硫酰胺酯的β-消除反应。该方法提供了便捷和直接获取多种N-Boc和N-PMB保护的β-芳氧-α-氨基酸，且具有完全的对映体纯度保留，产率中等到高。
• A facile synthesis of the spiroindoline-based growth hormone secretagogue, MK-677
  作者：Xian Liang Qi、Er Qun Yang、Jun Tao Zhang、Tao Wang、Xiao Ping Cao

  DOI：10.1016/j.cclet.2012.03.032

  日期：2012.6

  Abstract A facile and improved route for the synthesis of the orally active spiroindoline-based growth hormone secretagogue, MK-677 was described. The key step adopted the Fischer indole/reduction strategy. The preparation of the key intermediates N-protected piperidine carboxaldehyde 5 and the N-Boc-O-benzyl- d -serine (2) are also optimized.

  摘要描述了一种合成基于口服活性螺环二氢吲哚的生长激素促分泌素MK-677的简便方法。关键步骤采用了菲舍尔吲哚/还原策略。还优化了关键中间体N-保护的哌啶羧醛5和N-Boc-O-苄基-d-丝氨酸（2）的制备。
• Cyclic AMP-specific phosphodiesterase inhibitors
  申请人：ICOS Corporation

  公开号：US06423710B1

  公开（公告）日：2002-07-23

  Novel pyrrolidine compounds that are potent and selective inhibitors of PDE4, as well as methods of making the same, are disclosed. Use of the compounds in the treatment of inflammatory diseases and other diseases involving elevated levels of cytokines, as well as central nervous system (CNS) disorders, also is disclosed.

  揭示了一种新型吡咯烷化合物，它们是PDE4的有效和选择性抑制剂，以及制备这些化合物的方法。还揭示了这些化合物在治疗炎症性疾病和其他涉及细胞因子水平升高的疾病，以及中枢神经系统（CNS）疾病中的用途。