N-(p-methoxybenzyl)-D-serine methyl ester | 153046-00-5

• 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: N-(p-methoxybenzyl)-D-serine methyl ester
• 英文别名: (R)-methyl 3-hydroxy-2-(4-methoxybenzylamino)propanoate；methyl (4-methoxybenzyl)-D-serinate；methyl 3-hydroxy-2-[(4-methoxyphenyl)methylamino]propanoate；methyl (2R)-3-hydroxy-2-[(4-methoxyphenyl)methylamino]propanoate
• CAS: 153046-00-5
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: HRGFWZFYDVIMBC-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(p-methoxybenzyl)-D-serine methyl ester 在 四甲基乙二胺 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 26.5h， 生成 (S)-1-(tert-butyldimethylsilyloxy)-N-(4-methoxybenzyl)but-3-en-2-amine
  参考文献：
  名称：

  A facile synthetic route to diazepinone derivatives via ring closing metathesis and its application for human cytidine deaminase inhibitors

  摘要：

  通过一种基于环闭合互变的新的合成方法，从α-氨基酸和氨基醇中制备了多种二氮杂庚烯酮衍生物。这些二氮杂庚烯酮与核糖衍生物偶联，生成新型二氮杂庚烯酮核苷。其中，(4R)-1-核糖基-4-甲基-3,4-二氢-1H-1,3-二氮杂庚烯-2(7H)-酮（3）对人细胞胞苷脱氨酶表现出显著的抑制作用（Ki = 145.97 ± 4.87 nM）。

  DOI：

  10.1039/c2cc35484e
• 作为产物：
  描述：

  (R)-3-Hydroxy-2-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-propionic acid methyl ester 在 sodium tetrahydroborate 作用下， 生成 N-(p-methoxybenzyl)-D-serine methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of β-amino alcohols: practical preparation of all four stereomers of N-PMB-protected sphingosine from l- and d-serine

  摘要：

  Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected alpha'-amino enone derivative 6, which was reduced with Zn(BH4)(2) to the corresponding anti-beta-amino alcohol in >96% de. On the other hand, N-PMB-N-Boc-protected alpha'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00147-0

文献信息

• Total Synthesis of (+)-Hyacinthacine A₁ Using a Chemoselective Cross-Benzoin Reaction and a Furan Photooxygenation–Amine Cyclization Strategy
  作者：Karnjit Parmar、Pouyan Haghshenas、Michel Gravel

  DOI：10.1021/acs.orglett.1c00090

  日期：2021.2.19

  We report the shortest synthesis of glycosidase inhibitor (+)-hyacinthacine A1 using a highly chemoselective N-heterocyclic carbene-catalyzed cross-benzoin reaction as well as a furan photooxygenation–amine cyclization strategy. This is the first such cyclization on a furylic alcohol, an unprecedented reaction due to the notorious instability of the formed intermediates. The photooxygenation strategy

  我们报告了使用高度化学选择性的 N-杂环卡宾催化的交叉安息香反应以及呋喃光氧化-胺环化策略合成糖苷酶抑制剂 (+)-风信子 A 1的最短时间。这是第一次在呋喃醇上进行此类环化，由于形成的中间体众所周知的不稳定性，这是一种前所未有的反应。光氧化策略最终被纳入一个三步一锅法，形成 (+)-风信子 A 1的必需吡咯里西啶框架。
• A concise stereoselective synthesis of orthogonally protected lanthionine and β-methyllanthionine
  作者：Steven L. Cobb、John C. Vederas

  DOI：10.1039/b618178c

  日期：——

  ribosomally synthesized peptides contain either one or both of the unusual amino acids meso-lanthionine (m-Lan) or beta-methyllanthionine (beta-MeLan). Nucleophilic ring opening of sulfamidates allows facile preparation of stereochemically pure derivatives of m-Lan and beta-MeLan with orthogonal protection for solid phase synthesis of lantibiotic analogues.

  乳酸菌素（如乳链菌肽）对大多数革兰氏阳性细菌具有活性，并构成一类重要的抗菌剂。这些核糖体合成的肽含有一种或两种以上的非正常氨基酸，即中-羊毛硫氨酸（m-Lan）或β-甲基羊毛硫氨酸（β-MeLan）。氨基磺酸盐的亲核开环使得可以轻松制备立体化学纯的m-Lan和β-MeLan衍生物，并具有正交保护用于羊毛硫抗生素类似物的固相合成。
• [EN] HETEROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2022049134A1

  公开（公告）日：2022-03-10

  The invention provides new heterocyclic compounds having the general formula (I) wherein B, C, L, X, Y, RL and R3 to R5 are as described herein, compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds.

  该发明提供了具有一般式(I)的新杂环化合物，其中B、C、L、X、Y、RL和R3至R5如本文所述，包括这些化合物的组合物、制造这些化合物的方法以及使用这些化合物的方法。
• A facile synthetic route to diazepinone derivatives via ring closing metathesis and its application for human cytidine deaminase inhibitors
  作者：Minkyoung Kim、Kondaji Gajulapati、Chorong Kim、Hwa Young Jung、Jail Goo、Kyeong Lee、Navneet Kaur、Hyo Jin Kang、Sang J. Chung、Yongseok Choi

  DOI：10.1039/c2cc35484e

  日期：——

  A variety of diazepinone derivatives were prepared from α-amino acids and amino alcohols by a new synthetic methodology based on ring closing metathesis as a key step. The diazepinones were coupled with ribose derivatives to afford novel diazepinone nucleosides. Among them, (4R)-1-ribosyl-4-methyl-3,4-dihydro-1H-1,3-diazepin-2(7H)-one (3) showed a potent inhibitory effect (Ki = 145.97 ± 4.87 nM) against human cytidine deaminase.

  通过一种基于环闭合互变的新的合成方法，从α-氨基酸和氨基醇中制备了多种二氮杂庚烯酮衍生物。这些二氮杂庚烯酮与核糖衍生物偶联，生成新型二氮杂庚烯酮核苷。其中，(4R)-1-核糖基-4-甲基-3,4-二氢-1H-1,3-二氮杂庚烯-2(7H)-酮（3）对人细胞胞苷脱氨酶表现出显著的抑制作用（Ki = 145.97 ± 4.87 nM）。
• Stereoselective synthesis of β-amino alcohols: practical preparation of all four stereomers of N-PMB-protected sphingosine from l- and d-serine
  作者：Sung-Kee Chung、Jae-Mok Lee

  DOI：10.1016/s0957-4166(99)00147-0

  日期：1999.4

  Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected alpha'-amino enone derivative 6, which was reduced with Zn(BH4)(2) to the corresponding anti-beta-amino alcohol in >96% de. On the other hand, N-PMB-N-Boc-protected alpha'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%. (C) 1999 Elsevier Science Ltd. All rights reserved.