prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-azido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate | 273944-58-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-azido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
• CAS: 273944-58-4
• 化学式: C₂₈H₃₂N₄O₉
• 分子量: 568.583
• InChiKey: YHQAJIJTGUBKKB-GDTYMAFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-azido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate 在 N-甲基吗啉 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 溶剂黄146 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.33h， 生成 N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester
  参考文献：
  名称：

  受保护的糖肽固相合成的一种简便的甲硅烷基接头策略：IL-2（1-10）的N末端片段的合成。

  摘要：

  通过使用新的甲硅烷基接头的固相方法合成了白介素2（1）的N末端糖基肽片段。将O甲硅烷基化的Fmoc–Thr–OAll连接到商用HMP树脂上，并通过Fmoc方案进行肽链延伸，以生成受保护的七肽（3-10），该七肽通过氟解从树脂上裂解下来并用作氨基组分进一步固结在固体载体上。另一方面，Fmoc-Thr（GalNAc）-OAll衍生物的6-羟基被连接基甲硅烷基化并连接到树脂上。在树脂上进行了脱芳基作用，与七肽（3-10）的缩合反应以及在N末端带有两个氨基酸的延伸。氟离子介导的裂解释放N-和来自固体支持物的C-保护的糖肽具有良好的效率。完全脱保护的糖肽也通过树脂上的脱甲硅烷基化和硅烷基醚键的酸性裂解而合成。

  DOI：

  10.1016/s0040-4020(00)00588-3
• 作为产物：
  描述：

  N-芴甲氧羰基-L-苏氨酸烯丙基酯 在 二氯二茂锆 、 4 A molecular sieve 、 silver perchlorate 、 硫脲 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-azido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
  参考文献：
  名称：

  An efficient access to protected disialylated glycohexaosyl threonine present on the leukosialin of activated T-lymphocytes

  摘要：

  The total synthesis of the threonine-linked core 2 class disialylated hexasaccharide in a completely protected form was accomplished for the first time. The L-threonine conjugate, N-(9-fluorenylmethoxycarbonyl)-O-{(5-acetomido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylanic acid)-(2 --> 3)-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1 --> 4)-2-acetamido-2-deoxy-3,6-di-O-benzyl-beta-D-glucopyranosyl-(1 --> 6)-[(5-acctamido-4,7,8,9-tetra-O-benzyl-3, 5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2 --> 3)-2,6-di-O-benzyl-beta-D-galactopyranosyl-(1 --> 3)]-2-acetamido-2-deoxy-alpha-D-galactopyranosyl-(1d --> 4c:1f --> 4e)-dilactone}-L-threonine allyl ester was synthesized via stereocontrolled glycosylations employing readily accessible monosaccharidic blocks; t-butyl-diphenylsilyl-2-azido-2-deoxy-3, 6-di-O-benzyl-beta-D-glucopyranose, N-(9-fluorenylmethoxycarbonyl)-O-(2-azir-butylditnethylsilyl-2-deoxy-alpha-D-galactopyranosyl)-L-threonine allyl ester, 8, 9 and N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-alpha-D-galactopyranosy;)-L-threonine allyl ester. For the introduction of the amino acid. the azide group was used to temporarily mask the amino group of GalNAc so as to obtain an alpha-glycosidic linkage without participation from the C-2 substituent. The threonine was attached to the sugar unit at the monosaccharide stage to avoid loss of oligosaccharide at a later stage. The Fmoc and allyl ester protected amino acid at the reducing end facilitates efficient glycopeptide synthesis on solid-phase support. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00313-4

文献信息

• The first total synthesis of the core class II disialylated hexasaccharide as a building block for glycopeptide synthesis
  作者：Latika Singh、Yuko Nakahara、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1016/s0040-4039(99)00605-x

  日期：1999.5

  The first total synthesis of the protected core class II sialylated glycosyl-Thr hexasaccharide (3), utilizing suitably protected building blocks 4, 5, 7 and 8 was accomplished. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A Facile Silyl Linker Strategy for the Solid-Phase Synthesis of Protected Glycopeptide: Synthesis of an N-Terminal Fragment of IL-2 (1–10)
  作者：Akira Ishii、Hironobu Hojo、Aki Kobayashi、Kazuhiko Nakamura、Yuko Nakahara、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1016/s0040-4020(00)00588-3

  日期：2000.8

  An N-terminal glycodecapeptide fragment of interleukin 2 (1) was synthesized by solid-phase method utilizing a new silyl linker. The O-silylated Fmoc–Thr–OAll was attached to the commercial HMP-resin and peptide chain elongation was performed by Fmoc protocol to produce a protected heptapeptide (3–10), which was cleaved from the resin by fluoridolysis and used as the amino component for further condensation

  通过使用新的甲硅烷基接头的固相方法合成了白介素2（1）的N末端糖基肽片段。将O甲硅烷基化的Fmoc–Thr–OAll连接到商用HMP树脂上，并通过Fmoc方案进行肽链延伸，以生成受保护的七肽（3-10），该七肽通过氟解从树脂上裂解下来并用作氨基组分进一步固结在固体载体上。另一方面，Fmoc-Thr（GalNAc）-OAll衍生物的6-羟基被连接基甲硅烷基化并连接到树脂上。在树脂上进行了脱芳基作用，与七肽（3-10）的缩合反应以及在N末端带有两个氨基酸的延伸。氟离子介导的裂解释放N-和来自固体支持物的C-保护的糖肽具有良好的效率。完全脱保护的糖肽也通过树脂上的脱甲硅烷基化和硅烷基醚键的酸性裂解而合成。
• An efficient access to protected disialylated glycohexaosyl threonine present on the leukosialin of activated T-lymphocytes
  作者：Latika Singh、Yuko Nakahara、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1016/s0008-6215(99)00313-4

  日期：2000.4

  The total synthesis of the threonine-linked core 2 class disialylated hexasaccharide in a completely protected form was accomplished for the first time. The L-threonine conjugate, N-(9-fluorenylmethoxycarbonyl)-O-(5-acetomido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylanic acid)-(2 --> 3)-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1 --> 4)-2-acetamido-2-deoxy-3,6-di-O-benzyl-beta-D-glucopyranosyl-(1 --> 6)-[(5-acctamido-4,7,8,9-tetra-O-benzyl-3, 5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2 --> 3)-2,6-di-O-benzyl-beta-D-galactopyranosyl-(1 --> 3)]-2-acetamido-2-deoxy-alpha-D-galactopyranosyl-(1d --> 4c:1f --> 4e)-dilactone}-L-threonine allyl ester was synthesized via stereocontrolled glycosylations employing readily accessible monosaccharidic blocks; t-butyl-diphenylsilyl-2-azido-2-deoxy-3, 6-di-O-benzyl-beta-D-glucopyranose, N-(9-fluorenylmethoxycarbonyl)-O-(2-azir-butylditnethylsilyl-2-deoxy-alpha-D-galactopyranosyl)-L-threonine allyl ester, 8, 9 and N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-alpha-D-galactopyranosy;)-L-threonine allyl ester. For the introduction of the amino acid. the azide group was used to temporarily mask the amino group of GalNAc so as to obtain an alpha-glycosidic linkage without participation from the C-2 substituent. The threonine was attached to the sugar unit at the monosaccharide stage to avoid loss of oligosaccharide at a later stage. The Fmoc and allyl ester protected amino acid at the reducing end facilitates efficient glycopeptide synthesis on solid-phase support. (C) 2000 Elsevier Science Ltd. All rights reserved.