N-phthaloyl-S-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-cysteine benzyl ester | 186040-79-9

• 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-phthaloyl-S-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-cysteine benzyl ester
• 英文别名: Kdgjythradrkpg-xojhwwbqsa-；benzyl (2R)-2-(1,3-dioxoisoindol-2-yl)-3-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]sulfanylpropanoate
• CAS: 186040-79-9
• 化学式: C₅₂H₄₉NO₉S
• 分子量: 864.028
• InChiKey: KDGJYTHRADRKPG-XOJHWWBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-phthaloyl-S-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-cysteine benzyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 14.0h， 以44%的产率得到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

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.