3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate | 144367-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
• 英文别名: [(4aR,6S,7R,8R,8aS)-7-(1,3-dioxoisoindol-2-yl)-2,2-dimethyl-8-prop-2-enoxycarbonyloxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl] 2,2,2-trichloroethanimidate
• CAS: 144367-27-1
• 化学式: C₂₃H₂₃Cl₃N₂O₉
• 分子量: 577.803
• InChiKey: WKAGLYRHYLXAOZ-HLTONANMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 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 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.67h， 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：

  4-methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 ammonium cerium(IV) nitrate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Stereocontrolled synthesis of hyaluronan tetrasaccharide

  摘要：

  A stereocontrolled synthesis of hyaluronan tetrasaccharide is described for th

  DOI：

  10.1016/s0040-4039(00)61248-0

文献信息

• Synthesis of hyaluronic acid-related di-, tri-, and tetra-saccharides having an N-acetylglucosamine residue at the reducing end
  作者：Ted M. Slaghek、Yoshiaki Nakahara、Tomoya Ogawa、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0008-6215(00)90971-6

  日期：1994.3

  The synthesis is reported of 4-methoxyphenyl O-(beta-D-glucopyranosyluronic acid)-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside (1), 4-methoxyphenyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->4)-O-(beta-D- glucopyranosyluronic acid)-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside (5), and 4-methoxyphenyl O-(beta-D-glucopyranosyluronic acid)-(1-->3)-O-(2-acetamido-2-deoxy-beta-D-glu

  据报道合成了4-甲氧基苯基O-（β-D-吡喃葡萄糖基糖醛酸）-（1→3）-2-乙酰氨基-2-脱氧β-D-吡喃葡萄糖苷（1），4-甲氧基苯基O-（ 2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）-（1-> 4）-O-（β-D-葡萄糖基吡喃糖醛酸）-（1-> 3）-2-乙酰氨基-2-脱氧- β-D-吡喃葡萄糖苷（5）和4-甲氧基苯基O-（β-D-吡喃葡萄糖基糖醛酸）-（1-> 3）-O-（2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）- （1-> 4）-O-（β-D-吡喃葡糖基糖醛酸）-（1-> 3）-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷（10）细胞外多糖透明质酸。将6-O-Levulinoyl-2,3,4-三-Op-甲苯甲酰基-α-D-吡喃葡萄糖基三氯乙酰亚胺酸酯（3）与4-甲氧基苯基2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta缩合-D-吡喃葡萄糖苷（4）。
• Synthesis of a tetrasaccharide fragment of hyaluronic acid having a glucuronic acid at the reducing end
  作者：Ted M. Slaghek、Teija K. Hyppönen、Tomoya Ogawa、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0040-4039(00)61517-4

  日期：1993.12

  A stereocontrolled synthesis of a tetrasaccharide fragment of hyaluronic acid, beta-p-methoxyphenylglycoside of beta-D-GlcNAc-(1-->4)-beta-D-GlcA-(1-->3)-beta-D-GlcNAc-(1-->4)-D-GlcA, is presented.
• Synthesis of hyaluronic acid related di- and tetra-saccharides having a glucuronic acid at the reducing end
  作者：Ted M. Slaghek、Teija K. Hyppönen、Tomoya Ogawa、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0957-4166(00)86307-7

  日期：1994.11

  The synthesis is reported of 4-methoxyphenyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->4)-beta-D-glucopyranosyluronic acid (1) and 4-methoxyphenyl O-2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->4)-O-(beta-D-glucopyranosyluronic acid)-(1-->3)-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)- (1-->4-beta-D-glucopyranosyluronic acid (5), which represent structural elements of hyaluronic acid. 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate (3) was condensed with 4-methoxyphenyl 6-O-levulinoyl-2,3-di-O-p-toluoyl-beta-D-glucopyranoside (4) in dichloromethane, using boron trifluoride etherate as a promoter, yielding 4-methoxyphenyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D- glucopyranosylyl)-(1-->4)6-O-levulinoyl-2,3-di-O-p-toluoyl-beta-D-glucopyranoside (2). Subsequent delevulinoylation, oxidation, complete deprotection, and N-acetylation gave 1. Coupling of 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido- beta-D-glucopyranosyl trichloroacetimidate (9) with 4, followed by de-allyloxycarbonylation of the obtained disaccharide derivative gave 4-methoxyphenyl O-(2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D- glucopyranosyl)-(1-->4)-6-O-levulinoyl-2,3-di-O-p-toloyl-beta-D-glucopyranoside (8). Demethoxyphenylation and subsequent imidation of 2 afforded O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D- glucopyranosyl)-(1-->4)-6-O-levulinoyl-2,3-di-O-p-toluoyl-alpha/beta-D-glucopyranosylucopyranosyl trichloroacetimidate (7). Condensation of 7 and 8 in dichloromethane, with trimethylsilyl trifluoromethanesulfonate as a promoter, gave tetrasaccharide derivative 15. Subsequent de-isopropylidenation, O-acetylation, delevulinoylation, oxidation, complete deprotection, and N-acetylation yielded 5.
• Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-β-d-glucosamine at the reducing end
  作者：Koen M. Halkes、Ted M. Slaghek、Teija K. Hyppönen、Peter H. Kruiskamp、Tomoya Ogawa、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0008-6215(98)00116-5

  日期：1998.5

  To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-0-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride. (C) 1998 Elsevier Science 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.