allyl 2-O-benzoyl-α-L-fucopyranoside | 286476-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-benzoyl-α-L-fucopyranoside
• 英文别名: [(2R,3S,4R,5S,6S)-4,5-dihydroxy-6-methyl-2-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 286476-61-7
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: PVERCIHXNNGZSL-OIUQYKKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2-O-benzoyl-α-L-fucopyranoside 在 吗啉 、 吡啶 、 四(三苯基膦)钯 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 对甲苯磺酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 2.92h， 生成 allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis and conjugation of a sulfated disaccharide involved in the aggregation process of the marine sponge Microciona prolifera

  摘要：

  The synthesis is reported of allyl (sodium 2-acetamido-2-deoxy-beta-D-glucopyranosyl 3-sulfate)-(1-->3)-alpha-L-fucopyranoside which represents an oligosaccharide fragment of the aggregation factor of the marine sponge Microciona prolifera. The title compound was obtained by coupling of 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with allyl 2,4-di-O-benzoyl-alpha-Lfucopyranoside, followed by de-isopropylidenation, acetylation, de-allyloxycarbonylation, sulfation, de-acylation, and finally N-acetylation. The allyl glycoside was eventually converted into a 3-(2-aminoethylthio)propyl glycoside and then coupled to bovine serum albumin (BSA) using diethyl squarate as the bivalent linker, yielding 8 hapten molecules per molecule of BSA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00585-6
• 作为产物：
  描述：

  allyl 3,4-O-isopropylidene-α-L-fucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 allyl 2-O-benzoyl-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis and conjugation of a sulfated disaccharide involved in the aggregation process of the marine sponge Microciona prolifera

  摘要：

  The synthesis is reported of allyl (sodium 2-acetamido-2-deoxy-beta-D-glucopyranosyl 3-sulfate)-(1-->3)-alpha-L-fucopyranoside which represents an oligosaccharide fragment of the aggregation factor of the marine sponge Microciona prolifera. The title compound was obtained by coupling of 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with allyl 2,4-di-O-benzoyl-alpha-Lfucopyranoside, followed by de-isopropylidenation, acetylation, de-allyloxycarbonylation, sulfation, de-acylation, and finally N-acetylation. The allyl glycoside was eventually converted into a 3-(2-aminoethylthio)propyl glycoside and then coupled to bovine serum albumin (BSA) using diethyl squarate as the bivalent linker, yielding 8 hapten molecules per molecule of BSA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00585-6

文献信息

• 2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products
  作者：Anna Banaszek、Vladimir Zaitsev

  DOI：10.1016/j.tetasy.2003.11.018

  日期：2004.1

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and conjugation of a sulfated disaccharide involved in the aggregation process of the marine sponge Microciona prolifera
  作者：Henricus J. Vermeer、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0957-4166(99)00585-6

  日期：2000.2

  The synthesis is reported of allyl (sodium 2-acetamido-2-deoxy-beta-D-glucopyranosyl 3-sulfate)-(1-->3)-alpha-L-fucopyranoside which represents an oligosaccharide fragment of the aggregation factor of the marine sponge Microciona prolifera. The title compound was obtained by coupling of 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with allyl 2,4-di-O-benzoyl-alpha-Lfucopyranoside, followed by de-isopropylidenation, acetylation, de-allyloxycarbonylation, sulfation, de-acylation, and finally N-acetylation. The allyl glycoside was eventually converted into a 3-(2-aminoethylthio)propyl glycoside and then coupled to bovine serum albumin (BSA) using diethyl squarate as the bivalent linker, yielding 8 hapten molecules per molecule of BSA. (C) 2000 Elsevier Science Ltd. All rights reserved.