Bpoc-Ser(Bu^t) | 47634-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Bpoc-Ser(Bu^t)
• 英文别名: Bpoc.Ser(tBu).OH；Bpoc-Ser(Bu^t)-OH；2-(p-Biphenylyl)-isopropyloxycarbonyl-O-tert.-butyl-serin；N-(((2-([1,1'-Biphenyl]-4-yl)propan-2-yl)oxy)carbonyl)-O-(tert-butyl)-L-serine；(2S)-3-[(2-methylpropan-2-yl)oxy]-2-[2-(4-phenylphenyl)propan-2-yloxycarbonylamino]propanoic acid
• CAS: 47634-33-3
• 化学式: C₂₃H₂₉NO₅
• 分子量: 399.487
• InChiKey: RKFLTEIFFLLOTG-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  Bpoc-Ser(Bu^t) 在 三甲基氯硅烷 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 生成 O-叔丁基-L-丝氨酸
  参考文献：
  名称：

  Selective deprotection of the N.alpha.-tert-butyloxycarbonyl group in solid phase peptide synthesis with chlorotrimethylsilane in phenol

  摘要：

  The repetitive deprotection of the N(alpha)-tert-butyloxycarbonyl group during solid phase peptide synthesis was found to be efficient and quantitative by the use of a mild new reagent containing 1 M chlorotrimethylsilane and 1 M phenol in dichloromethane. Kinetic studies showed that the half-life for the reaction at 22-degrees-C with Boc-Val-resin was 17.5 min, a 40-fold increase over the rate in the absence of phenol. The reaction is not due to the presence of HCI in the reagent. The selectivity between the removal of the N(alpha)-tert-butyloxycarbonyl group and benzylic esters, ethers, and carbonate side chain protecting groups was >10(5) and relative to the anchoring benzyl ester bond to the resin support it was 6 X 10(3). This is a marked improvement over the selectivity of the conventional 50% trifluoroacetic acid in CH2Cl2 deprotecting agent and significantly reduces the accumulated byproducts resulting from losses of benzylic groups. The cleavage of the tert-butyl urethane was first order in Me3SiCl and second order in C6HrOH. The preferred reagent is 1 M Me3SiCl-3 M C6H5OH-CH2Cl2 and the deprotection time is 20 min (t1/2 = 1.8 min for Boc-Val-OCH2-resin). Evidence for the mechanism of the reaction was deduced. Several peptides, including Leu-enkephalin, [valine-5]-angiotensin II, and glucagon were successfully synthesized in high yields and excellent purity by the stepwise solid phase method using this new reagent.

  DOI：

  10.1021/jo00071a028
• 作为产物：
  描述：

  2-(4-联苯基)-2-丙醇 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 Bpoc-Ser(Bu^t)
  参考文献：
  名称：

  Schnabel,E. et al., Justus Liebigs Annalen der Chemie, 1971, vol. 743, p. 69 - 76

  摘要：

  DOI：

文献信息

• Tritiated peptides. Part 11. Synthesis of [4-3H-Phe6]-, [4-3H-Phe11]-, and [4-3H-Phe6,11]-somatostatin and the metabolite [des-Ala1]-somatostatin
  作者：Mark C. Allen、Derek E. Brundish、John R. Martin、Roy Wade

  DOI：10.1039/p19810002040

  日期：——

  ion-exchange and high-pressure liquid chromatography, and by enzymic digestion of the products modified by reduction and aminoethylation. The synthesis of the metabolite [des-Ala1]-somatostatin is described. The syntheses of [Phe(I)6]-, [Phe(I)11]- and [Phe(I)6,11]-somatostatin are described.

  合成方法描述了生长抑素+在位置6和11的苯丙氨酸残基中分别用tri标记，在残基6和11处分别用by标记，分别通过完全保护的还原性碘化反应使比放射性活度分别为15.5、13.8和14.1 Cim mol –1。前体。半胱氨酸残基受S-三苯甲基保护，二硫键由碘化oxidation化的受保护前体形成。通过酸性水解，离子交换和高压液相色谱，以及通过酶消化经还原和氨乙基化改性的产物，评估产物的纯度。描述了代谢物[des-Ala 1 ]-生长抑素的合成。[Phe（描述了I）6 ]-，[Phe（I）11 ]-和[Phe（I）6,11 ]-生长抑素。
• Peptides—XXXIX
  作者：I.J. Galpin、B.K. Handa、G.W. Kenner、S.R. Ohlsen、R. Ramage

  DOI：10.1016/0040-4020(80)80119-0

  日期：1980.1

  The synthesis of the fully protected octadecapeptide fragment (50–67) was achieved by combination of the subfragments 50–54,55–60 and 61–67. Single routes to two of these fragments are described but the fragment (55–60) was prepared by two different approaches. In this case salt-coupling techniques alleviated serious solubility problems. Fragment couplings were achieved using DCCI/HONSu.

  完整保护的十八肽片段（50-67）的合成通过亚片段50-54、55-60和61-67的组合实现。描述了到达其中两个片段的单条途径，但片段（55-60）是通过两种不同的方法制备的。在这种情况下，盐偶联技术可缓解严重的溶解性问题。使用DCCI / HONSu实现片段偶联。
• Peptides-XXXXV
  作者：I.J. Galpin、G.W. Kenner、R. Ramage、W.D. Thorpe

  DOI：10.1016/s0040-4020(01)98919-7

  日期：1981.1
• Thyrocalcitonin V.. Synthese und Charakterisierung des gesch�tzten Aufbaufragments ?-Thyrocalcitonin-(1-9)-nonapeptid
  作者：B. Kamber、W. Rittel

  DOI：10.1002/hlca.19690520421

  日期：——

  AbstractIn the recently [1] [4] described synthesis of the hypocalcaemic hormone α‐thyrocalcitonin (I) isolated from porcine thyroid glands, the protected nonapeptide sequence 1–9, represented an important intermediate. The present report describes in detail the synthesis of III in which the disulfide ring present in I is already formed. Fragment coupling of the sequences 1–4 and 5–9 led to the protected open chain intermediate Boc‐Cys(Trt)‐Ser(But)‐Asn‐Leu‐Ser(But)‐Thr(But)‐Cys(Trt)‐Val‐Leu‐OH which was obtained in cristalline form. After removal of the protecting S‐trityl groups by mercury acetate as described by ZERVAS, et al. [5], ring closure leading to III was effected by means of diiodoethane according to WEYGAND & ZUMACH [6]. Purification of III was achieved by counter current distribution. Removal of protecting groups by trifluoroacetic acid gave the free α‐thyrocalcitonin‐(1–9)‐nonapeptide IV, which was devoid of biological activity.