N-(9-fluorenylmethoxycarbonyl)-Ni-(butoxycarbonyl)-L-tryptophanyl-L-proline allyl ester | 475101-69-0

• 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-(9-fluorenylmethoxycarbonyl)-Ni-(butoxycarbonyl)-L-tryptophanyl-L-proline allyl ester
• 英文别名: N-(9-fluorenylmethoxycarbonyl)-Nⁱ-(butoxycarbonyl)-L-tryptophanyl-L-proline allyl ester
• CAS: 475101-69-0
• 化学式: C₃₉H₄₁N₃O₇
• 分子量: 663.77
• InChiKey: KYMDYGPNYHOKMY-TWJUONSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  49.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  116.17
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-Ni-(butoxycarbonyl)-L-tryptophanyl-L-proline allyl ester 在 四(三苯基膦)钯 吗啉 、 WSCD*HCl 、 1-羟基苯并三唑 、 三乙胺 、 N-甲基苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 H-Trp(Boc)-Pro-Asp(OtBu)-Gly-OtBu
  参考文献：
  名称：

  Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase

  摘要：

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.

  DOI：

  10.1080/07328300701296810
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-proline allyl ester 在 吗啉 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-(9-fluorenylmethoxycarbonyl)-Ni-(butoxycarbonyl)-L-tryptophanyl-L-proline allyl ester
  参考文献：
  名称：

  Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase

  摘要：

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.

  DOI：

  10.1080/07328300701296810

文献信息

• Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin
  作者：Jun-ichi Tamura、Akihiro Yamaguchi、Junko Tanaka

  DOI：10.1016/s0960-894x(02)00327-x

  日期：2002.8

  Tetraosyl hexapeptide, a part of the sequence of betaglycan: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stereocontrolled manner. (C) 2002 Elsevier Science Ltd. All rights reserved.