(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 | 186040-76-6

• 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: (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
• 英文别名: benzyl (2R)-2-(1,3-dioxoisoindol-2-yl)-3-[[(2R)-2-(1,3-dioxoisoindol-2-yl)-3-oxo-3-phenylmethoxypropyl]disulfanyl]propanoate
• CAS: 186040-76-6
• 化学式: C₃₆H₂₈N₂O₈S₂
• 分子量: 680.759
• InChiKey: MELXYIMMLYBPMD-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  178
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  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 三氟化硼乙醚 、 三乙基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 N-phthaloyl-S-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-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
• 作为产物：
  描述：

  N,N-diphthaloyl-L,L-cystine 、 氯化苄 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以71%的产率得到(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
  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

• Synthesis ofS-α-D-GlucosylatedL-Cysteine – A NovelS-Glycosyl Amino Acid
  作者：Ludwig Käsbeck、Horst Kessler

  DOI：10.1002/jlac.199719970123

  日期：1997.1

  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.