5-O-ethoxycarbonyl 1-O-methyl (2S)-2-(phenylmethoxycarbonylamino)pentanedioate | 117836-15-4

• 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: 5-O-ethoxycarbonyl 1-O-methyl (2S)-2-(phenylmethoxycarbonylamino)pentanedioate
• CAS: 117836-15-4
• 化学式: C₁₇H₂₁NO₈
• 分子量: 367.356
• InChiKey: JIULMWDYNACDPC-ZDUSSCGKSA-N

物化性质

• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-O-ethoxycarbonyl 1-O-methyl (2S)-2-(phenylmethoxycarbonylamino)pentanedioate 在 2,6-二甲基吡啶 、 chromium(VI) oxide 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 氢氟酸 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2S,5S)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid
  参考文献：
  名称：

  由（L）-谷氨酸手性合成5-羟基-（L）-哌酸

  摘要：

  DOI：

  10.1016/s0040-4039(00)86719-2
• 作为产物：
  描述：

  N²-benzyloxycarbonyl-L-glutamine methyl ester 在 亚硝酸特丁酯 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 5-O-ethoxycarbonyl 1-O-methyl (2S)-2-(phenylmethoxycarbonylamino)pentanedioate
  参考文献：
  名称：

  An efficient route to the α-methyl ester ofL-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid

  摘要：

  The treatment of the N-benzyloxycarbonyl alpha-methyl esters of L-glutamine or L-asparagine with tert-butyl nitrite in refluxing acetonitrile results-in selective hydrolysis of the amide group, giving optically pure Z-Glu-OMe (74%) or Z-Asp-OMe (88%); these are versatile chiral building blocks, and an efficient synthesis of cis-5-hydroxy-L pipecolic acid from Z-Glu-OMe is described.

  DOI：

  10.1039/cc9960000349

文献信息

• Synthesis and effect on gastric secretion of several di-or tripeptides related to proglumide.
  作者：KOJI IUCHI、MASAHIRO NITTA、KEIZO ITO、KOICHI SHIMOHARA、GORO TSUKAMOT

  DOI：10.1248/cpb.36.3961

  日期：——

  Several N-acyl di-or tripeptides related to proglumide (PhCO-DL-Glu-NPr2) were prepared and their effects on gastric secretion were examined by intraperitoneal injection in rats. PhCOGlu (Phe-NH2)-NPr2, Z-Glu (Phe-NH2)-NPr2, PhCO-Glu (NPr2)-Phe-NH2 and PhCO-Asp-(Phe-NH2)-NPr2 inhibited gastric secretion, while PhCO-Glu (Asp-Phe-NH2)-NPr2 stimulated gastric secretion. Of these peptides, PhCO-Glu (Phe-NH2)-NPr2 showed the most potent inhibitory activity against gastric secretion, and was more potent than proglumide.

  与普洛古米德（PhCO-DL-Glu-NPr2）相关的几种N-酰二肽或三肽被制备，并通过腹腔注射在大鼠身上检查其对胃分泌的影响。PhCOGlu（Phe-NH2）-NPr2、Z-Glu（Phe-NH2）-NPr2、PhCO-Glu（NPr2）-Phe-NH2和PhCO-Asp-(Phe-NH2)-NPr2抑制胃分泌，而PhCO-Glu（Asp-Phe-NH2）-NPr2则刺激胃分泌。在这些肽中，PhCO-Glu（Phe-NH2）-NPr2对胃分泌表现出最强的抑制活性，其效力超过普洛古米德。
• Synthesis of (S)-2-amino-8-oxodecanoic acid (Aoda) and apicidin A
  作者：Liyuan Mou、Gurdial Singh

  DOI：10.1016/s0040-4039(01)01331-4

  日期：2001.9

  The synthesis of (S)-2-amino-8-oxodecanoic acid, a constituent of the cyclic tetrapeptides, the apicidins, was accomplished under photolytic conditions in the presence of tri-n-butyltin hydride using glutamic acid. This enabled a total synthesis of apicidin A to be completed.

  的合成（小号）-2-氨基-8- oxodecanoic酸时，环状四肽的组成部分，apicidins，被光解条件下，在三-的存在下完成Ñ使用谷氨酸-butyltin氢化物。这使得能够完成阿皮定A的总合成。
• Synthesis of [6-13C]-L-lysine
  作者：Andrew Sutherland、Christine L. Willis

  DOI：10.1002/(sici)1099-1344(199601)38:1<95::aid-jlcr816>3.0.co;2-q

  日期：1996.1

  A short and efficient enantioselective synthesis of [6- 13 C]-L-lysine from commercially available N-benzyloxycarbonyl-L-glutamic acid α-methyl ester is described using [ 13 C]-sodium cyanide as the source of isotopic label.

  使用[ 13 C]-氰化钠作为同位素标记的来源，描述了从市售的N-苄氧羰基-L-谷氨酸α-甲基酯短而有效的对映选择性合成[6- 13 C]-L-赖氨酸。
• Diastereoselective synthesis of cyclic β2,3-amino acids utilizing 4-substituted-1,3-oxazinan-6-ones
  作者：Brad E. Sleebs、Nghi H. Nguyen、Andrew B. Hughes

  DOI：10.1016/j.tet.2013.05.016

  日期：2013.7

  The 4-substituted-1,3-oxazinan-6-one scaffold is a versatile synthon enabling access to a diverse array of beta-amino acid derivatives. In this study, the synthetic utility of the 1,3-oxazinan-6-one is expanded to include the diastereoselective synthesis of cyclic beta(2,3)-amino acids. Enolate chemistry is used to first alkylate the 4-vinyl, 4-allyl, and 4-butenyl oxazinan-6-ones with various alkenyl electrophiles, in high dr. The resulting 4,5-bis-alkene adducts are then transformed into 4,5-cyclic-1,3-oxazinan-6-ones utilizing the ring closing metathesis reaction. The metathesis products are subsequently converted into a variety of five-, six-, and seven-membered cyclic beta(2,3)-amino acids. The research further highlights the 1,3-oxazinan-6-one as a versatile synthon for producing beta-amino acid derivatives. (C) 2013 Elsevier Ltd. All rights reserved.
• Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines:  New Reagents for Guanidinylation Reactions
  作者：Konrad Feichtinger、Heather L. Sings、Tracy J. Baker、Kenneth Matthews、Murray Goodman

  DOI：10.1021/jo9814344

  日期：1998.11.1

  New guanidinylation reagents are reported. These reagents consist of N,N',N "-tri-Boc-guanidine (1) and N,N',N "-tri-Cbz-guanidine (2), which allow for the facile conversion of alcohols to substituted guanidines. A series of arginine analogues were synthesized via condensation of a primary or secondary alcohol with the guanidinylation reagents 1 or 2, under Mitsunobu conditions,(1) to produce protected alkylated guanidines. In addition, an extended study of the previously reported reagents(2) N,N'-di-Boc-N "-triflylguanidine (3) and N,N'-di-Cbz-N "-triflylguanidine (4) is presented. The triflyldiurethane-protected guanidine 3 was utilized to guanidinylate primary and secondary amines under mild conditions with high yield in both solution and on solid phase.