N-phthaloyl-S-(α-D-glucopyranosyl)-L-cysteine | 186040-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-phthaloyl-S-(α-D-glucopyranosyl)-L-cysteine
• 英文别名: (2R)-2-(1,3-dioxoisoindol-2-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpropanoic acid
• CAS: 186040-80-2
• 化学式: C₁₇H₁₉NO₉S
• 分子量: 413.405
• InChiKey: ZQMVUKVRPQOYOB-RAXYOVQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  190
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-phthaloyl-S-(α-D-glucopyranosyl)-L-cysteine 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 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：

  2,3,4,6-四-O-苯基-Alpha-D-吡喃葡萄糖基三氯乙酰亚氨酸 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

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.