Boc-L-Thr-OH | 2592-18-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苏氨酸类衍生物
• 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
• 英文名称: Boc-L-Thr-OH
• 英文别名: t-Butoxycarbonyl-L-threonin；(2R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 2592-18-9；23082-29-3；23082-30-6；55674-67-4；85979-33-5；86748-77-8
• 化学式: C₉H₁₇NO₅
• 分子量: 219.238
• InChiKey: LLHOYOCAAURYRL-PRJDIBJQSA-N

物化性质

• 熔点：
  80-82 °C(lit.)
• 比旋光度：
  -8.5 º (c=1, acetic acid)
• 沸点：
  360.05°C (rough estimate)
• 密度：
  1.2470 (rough estimate)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  29241990
• 危险品运输编号：
  OTH
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

用途

Boc-L-苏氨酸是一种氨基酸衍生物，可用作生化试剂。

应用

Boc-L-苏氨酸主要应用于多肽合成，并广泛用于多种药物以及生物技术领域。苏氨酸因其广泛的用途和作用，在现有技术中常将Boc作为保护基对L-苏氨酸进行保护处理。Boc-L-苏氨酸已成为多种医药和生物科技的重要中间原料。

制备

1. 将15.8 g L-苏氨酸加入200 ml 0.0005 mol/L 碳酸氢钾溶液中搅拌溶解，再分三次分别加入8 g (Boc)₂O，每次反应2小时。

2. 反应结束后，用0.001 mol/L 盐酸调节pH至3，然后使用醋酸叔丁酯（0.4 L/次）萃取产品三次。合并酯层后，用盐水洗涤直至中性，加入15克无水硫酸钠干燥8小时。

3. 过滤后，减压浓缩滤液，加入50 ml 石油醚搅拌结晶。离心出产物并烘干，最终得到22.4 g产品，产率为91.73%。

反应信息

• 作为反应物：
  描述：

  (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 、 Boc-L-Thr-OH 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Discovery of (R)-1-(3-(4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)-2-(dimethylamino)ethanone (CHMFL-FLT3-122) as a Potent and Orally Available FLT3 Kinase Inhibitor for FLT3-ITD Positive Acute Myeloid Leukemia

  摘要：

  FLT3-ITD mutant has been observed in about 30% of AML patients and extensively studied as a drug discovery target. On the basis of the structure of PCI-32765 (ibrutinib), a BTK kinase inhibitor that was recently reported to bear FLT3 kinase activity through a structure-guided drug design approach, we have discovered compound 18 (CHMFL-FLT3-122), which displayed an IC50 of 40 nM against FLT3 kinase and achieved selectivity over BTK kinase (over 10-fold). It significantly inhibited the proliferation of FLT3-ITD positive AML cancer cell lines MV4-11 (GI(50) = 22 nM), MOLM13/14 (GI(50) = 21 nM/42 nM). More importantly, 18 demonstrated 170-fold selectivity between FLT3 kinase and c-KIT kinase (GI50 = 11 nM versus 1900 nM) in the TEL-fusion isogenic BaF3 cells indicating a potential to avoid the FLT3/c-KIT dual inhibition induced myelosuppression toxicity. In the cellular context it strongly affected FLT3-ITD mediated signaling pathways and induced apoptosis by arresting the cell cycle into the G0/G1 phase. In the in vivo studies 18 demonstrated a good bioavailability (30%) and significantly suppressed the tumor growth in MV4-11 cell inoculated xenograft model (50 mg/kg) without exhibiting obvious toxicity. Compound 18 might be a potential drug candidate for FLT3-ITD positive AML.

  DOI：

  10.1021/acs.jmedchem.5b01611

文献信息

• LANTHANIDE CLUSTERS AND METHODS OF USE THEREOF
  申请人：YEDA RESEARCH AND DEVELOPMENT CO. LTD.

  公开号：US20160002269A1

  公开（公告）日：2016-01-07

  The present invention is directed to multinuclear lanthanides chiral clusters, based on phenyl-oxazoline-amide (POxA) ligands, and to methods of use thereof. The chiral clusters of this invention are highly fluorescent with high stability.

  本发明涉及基于苯基-噁唑啉酰胺（POxA）配体的多核镧系手性簇以及其使用方法。本发明的手性簇具有高荧光性能和高稳定性。
• [EN] NOVEL PHTHALAZINONE-PYRROLOPYRIMIDINECARBOXAMIDE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE PHTALAZINONE-PYRROLOPYRIMIDINECARBOXAMIDE
  申请人：NYCOMED GMBH

  公开号：WO2012171900A1

  公开（公告）日：2012-12-20

  The compounds of formula (1), in which R1, R7, R8, R9, R10, R17, R18, R19, R20 and m have the meanings as given in the description, are novel effective inhibitors of type 4 and 5 phosphodiesterase.

  式（1）中的化合物，其中R1、R7、R8、R9、R10、R17、R18、R19、R20和m的含义如描述中所述，是新颖的有效的4型和5型磷酸二酯酶抑制剂。
• NOVEL PHTHALAZINONE-PYRROLOPYRIMIDINECARBOXAMIDE DERIVATIVES
  申请人：Stengel Thomas

  公开号：US20140112945A1

  公开（公告）日：2014-04-24

  The compounds of formula (1) in which R1, R7, R8, R9, R10, R17, R18, R19, R20 and m have the meanings as given in the description, are novel effective inhibitors of type 4 and type 5 phosphodiesterase.

  式（1）中的化合物，其中R1、R7、R8、R9、R10、R17、R18、R19、R20和m的含义如描述中所述，是新颖的有效的磷酸二酯酶4型和5型抑制剂。
• Parallel solid phase synthesis of tetrasubstituted diethylenetriamines via selective amide alkylation and exhaustive reduction of N-acylated dipeptides
  作者：Adel Nefzi、John M. Ostresh、Richard A. Houghten

  DOI：10.1016/s0040-4020(98)01043-6

  日期：1999.1

  Polyamines are a rapidly developing area of vital importance to biomedical science. Selective N-alkylation followed by N-terminal acylation and the complete reduction of carbonyl amide bonds enables the preparation by parallel solid phase synthesis of a wide range of N1,N5,1,4-tetrasubstituted-1,5-diamino-3-azapentane derivatives.

  多胺是对生物医学至关重要的快速发展领域。选择性的N-烷基化，接着通过N-末端酰化和的羰酰胺键的完全降低使得能够通过宽范围的N个并行固相合成制备1，N 5，1,4-四取代-1,5-二氨基-3- -氮杂戊烷衍生物。
• First Total Synthesis and Biological Potential of a Heptacyclopeptide of Plant Origin
  作者：Rajiv Dahiya、Sunil Singh

  DOI：10.1002/cjoc.201600419

  日期：2016.11

  Synthesis of a natural glycine‐rich heptacyclopeptide ‐ mahafacyclin A (7) was accomplished by solution‐phase technique of peptide synthesis via coupling of tetrapeptide unit Boc‐L‐Thr‐L‐Ile‐L‐Leu‐Gly‐OH with tripeptide unit L‐Val‐L‐Phe‐Gly‐OMe followed by cyclization of linear heptapeptide fragment. Structure of the newly synthesized cyclopolypeptide was confirmed by means of chemical, spectroscopic

  天然富含甘氨酸的heptacyclopeptide的合成- （mahafacyclin阿7）通过的肽合成溶液相技术来完成经由四肽单元的Boc-的耦合大号-Thr-大号-Ile-大号-Leu酰-Gly-OH与三肽单元大号-Val - L -Phe-Gly-OMe，然后环化线性七肽片段。通过化学，光谱分析证实了新合成的环多肽的结构，并进行了抗菌，抗真菌和驱虫活性研究。生物活性结果显示对皮肤癣菌的合成肽的抗真菌和抗蠕虫活性须发癣菌，M. audouinii和worm种M. konkanensis，P. corethruses和E. eugeniea。