[(5S)-5-[[(叔丁基氧基)羰基]氨基]-6-羟基己基]氨基甲酸苄酯 | 82689-20-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [(5S)-5-[[(叔丁基氧基)羰基]氨基]-6-羟基己基]氨基甲酸苄酯
• 中文别名: (S)-叔丁基苄基(6-羟基己烷-1,5-二基)二氨基甲酸酯
• 英文名称: Boc-Lys(Z)-ol
• 英文别名: (S)-BOC-lysinol(Z)；(2S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylaminohexan-1-ol；Boc-L-Lys(Z)-alcohol；N⁶-benzyloxycarbonyl-N²-tert-butoxycarbonyl-L-lysinol；benzyl (5S)-5-{[(tert-butyloxy)carbonyl]amino}-6-hydroxyhexylcarbamate；benzyl {(5S)-5-[(tert-butoxycarbonyl)amino]-6-hydroxyhexyl}carbamate；N-Boc-Lys(Cbz)-ol；Boc-l-Lys(Z)-ol；(S)-Benzyl tert-butyl (6-hydroxyhexane-1,5-diyl)dicarbamate；benzyl N-[(5S)-6-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]carbamate
• CAS: 82689-20-1
• 化学式: C₁₉H₃₀N₂O₅
• 分子量: 366.458
• InChiKey: MLAPMZGXJGUYNO-INIZCTEOSA-N

物化性质

• 熔点：
  62-63℃
• 沸点：
  551.4±50.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Boc-L-Lys(Z)-OL
Synonyms: Boc-L-Lysinol(Z) (2S)-6-(Benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-1-hexanol

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: Boc-L-Lys(Z)-OL
CAS number: 82689-20-1

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C19H30N2O5
Molecular weight: 366.5

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  [(5S)-5-[[(叔丁基氧基)羰基]氨基]-6-羟基己基]氨基甲酸苄酯 在 三乙胺 、 乙酰氯 作用下， 以 二甲基亚砜 为溶剂， 反应 12.67h， 生成
  参考文献：
  名称：

  基于哌啶-哌啶酮的多方面二级结构模拟物

  摘要：

  极简二级结构模拟物通常被制成类似于蛋白质-蛋白质相互作用 (PPI) 中的一个界面，从而扰乱它。我们最近提出合适的化学型可以直接与界面区域匹配，而无需考虑二级结构。在这里，我们描述了新化学型1的模块化合成，其溶液态构象集合的模拟，以及与理想二级结构和 PPI 中真实界面区域的相关性。脚手架1呈现彼此完全分离的氨基酸侧链，其方向与理想的片状或螺旋结构非常相似，在 PPI 界面具有相似的非理想结构，以及其他 PPI 界面的模拟构象与任何二级结构不相似的区域. 68 种不同的 PPI，其中1 个匹配孔的构象被识别。还提出了一种新方法来确定极简模拟晶体结构与其溶液构象的相关性。因此，dld - 1 faf以比最小能量溶液状态高0.91 kcal mol -1的构象结晶。

  DOI：

  10.1002/anie.201400927
• 作为产物：
  描述：

  N6-((苄氧基)羰基)-N2-(叔丁氧基羰基)-L-赖氨酸甲酯 在 sodium tetrahydroborate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 [(5S)-5-[[(叔丁基氧基)羰基]氨基]-6-羟基己基]氨基甲酸苄酯
  参考文献：
  名称：

  New methods and reagents in organic synthesis, 29, A practical method for the preparation of optically acive N-protected .ALPHA.-amino aldehydes and peptide aldehydes.

  摘要：

  高度光学活性的N-保护的α-氨基酸醛和肽醛可以通过使用硫三氧化物-吡啶复合物和二甲基亚砜的组合，在三乙胺存在下，从相应的β-氨基酸醇方便地制备，且几乎或完全不发生消旋化。

  DOI：

  10.1248/cpb.30.1921

文献信息

• An expedient route for the reduction of carboxylic acids to alcohols employing 1-propanephosphonic acid cyclic anhydride as acid activator
  作者：G. Nagendra、C. Madhu、T.M. Vishwanatha、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2012.06.108

  日期：2012.9

  method for the synthesis of alcohols from the corresponding carboxylic acids is described. Activation of carboxylic acid with 1-propanephosphonic acid cyclic anhydride (T3P) and subsequent reduction using NaBH4 yield the alcohol in excellent yields with good purity. Reduction of several alkyl/aryl carboxylic acids and Nα-protected amino acids/peptide acids as well as Nβ-protected amino acids was successfully

  描述了一种由相应的羧酸合成醇的简单有效的方法。用1-丙烷膦酸环酐（T3P）活化羧酸，然后使用NaBH 4还原，可得到纯度高，纯度高的醇。的减少几个烷基/芳基羧酸和N α -保护的氨基酸/肽酸以及如N β -保护的氨基酸被成功地执行，以获得良好的收率相应的醇。所有产物均通过1 H NMR和质谱分析充分表征。该过程温和，简单，并且容易分离产物。
• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Synthesis and Characterization of Optically Pure Gamma‐ <scp>PNA</scp> Backbones by <scp>SIBX</scp> ‐Mediated Reductive Amination
  作者：Alagarsamy Periyalagan、Yong‐Tae Kim、In Seok Hong

  DOI：10.1002/bkcs.12365

  日期：2021.10

  Therefore, the synthesis of an optically pure γ-backbone is very important. Here, we report a novel synthetic strategy for the suppression of epimerization during the synthesis of the γ-PNA backbone. A stabilized form of 2-iodoxybenzoic acid (SIBX) was used as an oxidative reagent in the key intermediate of the N-Boc-amino acetaldehyde synthesis. This paper reports (1) the synthesis and comparison

  手性肽核酸 (PNA) 是常规 PNA 的衍生物，通过在其骨架上引入手性中心，并且已知比常规 PNA 与 DNA 或 RNA 的结合更强。特别是，在 γ-骨架的情况下，L异构体稳定 PNA/DNA 双链，而D-异构体具有相反的作用。因此，合成光学纯的γ-主链是非常重要的。在这里，我们报告了一种新的合成策略，用于在 γ-PNA 主链的合成过程中抑制差向异构化。稳定形式的 2-碘氧基苯甲酸 (SIBX) 在 N-Boc-氨基乙醛合成的关键中间体中用作氧化试剂。本文报道了 (1) 三种不同的 γ-PNA 骨架 (赖氨酸、丙氨酸和谷氨酸) 通过三种不同的合成路线 (SIBX、氢化铝锂和 Red-Al) 的合成和比较和 (2) 手性的测定其衍生化合物的纯度。SIBX 介导的 γ-PNA 骨架的对映体过量纯度被确定为超过 99.4%，由标准 RP-C18 柱上的高效液相色谱 (HPLC) 色谱图确定。它相对高于本工作中检查的其他方法。
• Synthesis and DNA-Damaging Properties of Cisplatin-<i>N</i>-Mustard Conjugates
  作者：Stefan Schiesser、Benjamin Hackner、Milan Vrabel、Wolfgang Beck、Thomas Carell

  DOI：10.1002/ejoc.201500144

  日期：2015.4

  We report the synthesis of two novel cisplatin-N-mustard conjugates. In these compounds two potentially DNA-damaging molecules are combined and are separated by a spacer containing either one or four ethylene glycol units. We have shown that these conjugates are capable of forming novel clustered DNA adducts, thereby strongly increasing the lesion density in double-stranded DNA, which is thought to

  我们报告了两种新型顺铂-N-芥末偶联物的合成。在这些化合物中，两个潜在的 DNA 损伤分子结合在一起，并被一个含有一个或四个乙二醇单元的间隔物隔开。我们已经证明这些缀合物能够形成新的成簇 DNA 加合物，从而大大增加双链 DNA 的损伤密度，这被认为会阻止 DNA 修复和跨损伤合成。它们抑制细胞分裂的能力在大肠杆菌试验中得到证实。
• A facile synthesis of chiral N-protected β-amino alcohols.
  作者：Marc Rodriguez、Muriel Llinares、Sylvie Doulut、Annie Heitz、Jean Martinez

  DOI：10.1016/s0040-4039(00)92121-x

  日期：1991.2

  Chiral N-protected β-amino alcohols are easily obtained by NaBH4 reduction of mixed anhydrides of N-protected α-amino acids in an organic/aqueous medium. The alcohols obtained from side chain or main chain reduction of N-protected aspartic acid are converted in good yields into lactones.

  通过在有机/水介质中通过NaBH 4还原N-保护的α-氨基酸的混合酸酐可以容易地获得手性的N-保护的β-氨基醇。由N-保护的天冬氨酸的侧链或主链还原得到的醇以良好的产率转化为内酯。