N-phthalyl-L-cysteine benzyl ester | 186038-72-2

• 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-phthalyl-L-cysteine benzyl ester
• 英文别名: benzyl (2R)-2-(1,3-dioxoisoindol-2-yl)-3-sulfanylpropanoate
• CAS: 186038-72-2
• 化学式: C₁₈H₁₅NO₄S
• 分子量: 341.387
• InChiKey: LJBIJXXERPGRHJ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-phthalyl-L-cysteine benzyl ester 在 palladium on activated charcoal 盐酸 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 反应 15.0h， 生成 N-phthaloyl-S-(α-D-glucopyranosyl)-L-cysteine
  参考文献：
  名称：

  Synthesis ofS-α-D-GlucosylatedL-Cysteine – A NovelS-Glycosyl Amino Acid

  摘要：

  AbstractWhereas S‐β‐D‐glucosylated L‐cysteine is easily available, the corresponding α‐anomer has not been prepared before. In this paper a solution to the synthetic problem is presented. The glycosylation of highly nucleophilic N‐phthaloyl‐L‐cysteine esters 4 and 5 with 2,3,4,6‐tetra‐O‐benzyl‐α‐L‐glucopyranosyl trichloroacetimidate in the presence of 1 equivalent of BF3 · Et2O provided the protected cysteinyl‐S‐α‐glycosides 6 and 7 in good yields. These S‐α‐glycosylated cysteine derivatives were only available by use of the non‐urethane N‐protected glycosyl acceptors 4 and 5. Palladium‐catalyzed hydrogenolysis and subsequent hydrazinolysis of the benzylated compound 7 afforded L‐cysteinyl‐S‐α‐D‐glucoside 1, a novel S‐glycosyl amino acid.

  DOI：

  10.1002/jlac.199719970123
• 作为产物：
  描述：

  (R)-3-[(R)-2-Benzyloxycarbonyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyldisulfanyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid benzyl ester 在 三乙基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以96%的产率得到N-phthalyl-L-cysteine benzyl ester
  参考文献：
  名称：

  Synthesis ofS-α-D-GlucosylatedL-Cysteine – A NovelS-Glycosyl Amino Acid

  摘要：

  AbstractWhereas S‐β‐D‐glucosylated L‐cysteine is easily available, the corresponding α‐anomer has not been prepared before. In this paper a solution to the synthetic problem is presented. The glycosylation of highly nucleophilic N‐phthaloyl‐L‐cysteine esters 4 and 5 with 2,3,4,6‐tetra‐O‐benzyl‐α‐L‐glucopyranosyl trichloroacetimidate in the presence of 1 equivalent of BF3 · Et2O provided the protected cysteinyl‐S‐α‐glycosides 6 and 7 in good yields. These S‐α‐glycosylated cysteine derivatives were only available by use of the non‐urethane N‐protected glycosyl acceptors 4 and 5. Palladium‐catalyzed hydrogenolysis and subsequent hydrazinolysis of the benzylated compound 7 afforded L‐cysteinyl‐S‐α‐D‐glucoside 1, a novel S‐glycosyl amino acid.

  DOI：

  10.1002/jlac.199719970123

文献信息

• Convenient Syntheses of 2,3,4,6-Tetra-O-AlkylatedD-Glucose andD-Galactose
  作者：Ludwig Käsbeck、Horst Kessler

  DOI：10.1002/jlac.199719970124

  日期：1997.1

  Convenient syntheses of the 2,3,4,6-tetra-O-benzylated and -allylated D-glucopyranoses 1 and 2 and the corresponding D-galactopyranoses 3 and 4 are described. The D-glucose derivatives 1 and 2 were obtained from inexpensive sucrose by peralkylation and subsequent acid hydrolysis. In this reaction sequence an alkylated D-fructofuranosyl cation is generated which was trapped by different nucleophiles

  描述了2,3,4,6-四-O-苄基化和烯丙基化的D-吡喃葡萄糖1和2以及相应的D-吡喃半乳糖3和4的方便的合成。D-葡萄糖衍生物1和2是从廉价的蔗糖中通过过烷基化和随后的酸水解获得的。在该反应序列中，产生烷基化的D-果糖呋喃糖基阳离子，该阳离子被不同的亲核试剂捕获，得到4-苄氧基亚甲基糠醛（8）和烷基化的D-果糖苷7、8和10。另一方面，2,3,4,6-四-O-苄基-D-半乳糖3通过用N-溴代琥珀酰亚胺水溶液氧化裂解乙基2,3,4,6-四-O-苄基-1-硫代-α，β-D-吡喃半乳糖苷（11）来合成。通过对甲氧基苄基β-D-葡糖苷制备2,3,4,6-四-O-烯丙基-D-吡喃葡萄糖苷（2）的替代途径吸引力较小。然而，被用于的2,3,4,6-四-合成此路线ö -allyl- d半乳糖（4）。
• Synthesis and Immunostimulating Activity of A Thioglycolipopeptide Glycomimetic As A Potential Anticancer Vaccine Derived From Tn Antigen
  作者：Ennio Bousquet、Angelo Spadaro、Maria S. Pappalardo、Renato Bernardini、Rosalba Romeo、Luigi Panza、Giuseppe Ronsisvalle

  DOI：10.1080/07328300008544097

  日期：2000.1

  sulphur atom (S-Tn). The S-Tn thioglycopeptide was linked to the P3CS immunoadjuvant to obtain the potential S-Tn vaccine. Moreover, we synthesized the natural Tn antigen and derivatized it similarly to obtain the Tn vaccine. Last, we evaluated the immunostimulating activity of the two synthetic potential vaccines in vitro using cultured mouse splenocytes. The S-Tn construct showed immunostimulating activity

  摘要Tn表位是与肿瘤相关的O-连接的细胞表面糖肽之一。它在超过70％的人类上皮癌中表达，例如肺癌，结肠癌，胃癌和乳腺癌。在糖苷酶存在下，可以化学或酶促方式裂解N-乙酰基半乳糖胺与丝氨酸或苏氨酸之间的Tn抗原的糖苷键。后一种情况在体内尤其是一个问题。因此，获得维持或改善后者的免疫原性的Tn抗原的代谢稳定的类似物将是非常令人感兴趣的。这项工作的目的是使用化学上和代谢上稳定的Tn抗原模拟糖来合成全合成疫苗，其中糖苷间的氧被硫原子（S-Tn）取代。将S-Tn硫糖肽与P3CS免疫佐剂连接以获得潜在的S-Tn疫苗。此外，我们合成了天然Tn抗原并将其类似地衍生化以获得Tn疫苗。最后，我们使用培养的小鼠脾细胞评估了两种合成潜在疫苗的体外免疫刺激活性。就最大应答而言，S-Tn构建体显示出与Tn类似物相当的免疫刺激活性。而且，由于其较高的稳定性，与Tn类似物相比，S-Tn构建体在较低剂量下达到了其最大作用。我