benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside | 33423-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside
• 英文别名: benzyl-(2-acetylamino-O³-benzoyl-2-deoxy-α-D-glucopyranoside)；Benzyl-(2-acetylamino-O³-benzoyl-2-desoxy-α-D-glucopyranosid)；benzyl 2-(acetylamino)-2-deoxy-3-O-(phenylcarbonyl)-alpha-D-glucopyranoside；[(2R,3S,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl] benzoate
• CAS: 33423-31-3
• 化学式: C₂₂H₂₅NO₇
• 分子量: 415.443
• InChiKey: MEMWJQGJQSNYKB-DOSYZEEDSA-N

物化性质

• 沸点：
  663.6±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside 在 sodium methylate 、 四氯化锡 作用下， 以 甲醇 为溶剂， 反应 18.25h， 生成 benzyl β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  One-pot synthesis of β-d-Gal>(1 → 4)[β-d-Galp(1 → 6)]-d-GlcNAc, a ‘core’ trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi

  摘要：

  Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (4) with penta-O-benzoyl-beta-D-galactopyranose (6) gave the derivative of beta-D-Galp-(1 --> 6)-alpha-D-GlcNAc 7 in 80% yield, This was glycosylated with penta-O-benzoyl-alpha,beta- D-galactofuranose (5>, employing the same catalyst, to afford the protected benzyl per-O-benzoyl-beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]D-GlcNAc 10 in 41% yield, Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). beta-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00256-5
• 作为产物：
  描述：

  benzyl-[2-acetylamino-O³-benzoyl-O⁴,O⁶-((Ξ)-benzylidene)-2-deoxy-α-D-glucopyranoside] 在 水 、 溶剂黄146 作用下， 生成 benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Kuhn et al., Justus Liebigs Annalen der Chemie, 1958, vol. 611, p. 236,239

  摘要：

  DOI：

文献信息

• Diastereoselective formation of pyruvylated glycosides from partly protected sugars and methyl pyruvate
  作者：Thomas Ziegler、Elisabeth Eckhardt、Gerhard Herold

  DOI：10.1016/s0040-4039(00)60097-7

  日期：1992.7

  Various partly protected sugars (gluco-, manno-, and galactopyranosides) were acetalized with methyl pyruvate in moderate to good yield with BF3-etherate as the condensing reagent. Thus, (1-methoxycarbonyl)ethylidene glycosides were obtained diastereoselectivity.

  各种部分受保护的糖（葡萄糖基，甘露糖苷和半乳糖吡喃糖苷）以丙酮酸甲酯缩醛化，并以BF 3-醚酸酯为缩合试剂。因此，获得了（1-甲氧基羰基）亚乙基糖苷的非对映选择性。
• Synthesis and biological activity of O-(N-acetyl-β-muramoyl-l-alanyl-d-isoglutamine)-(1→6)-2-acylamino-2-deoxy-d-glucoses
  作者：Akira Hasegawa、Masahiko Ozaki、Yasuhiko Goh、Makoto Kiso、Ichiro Azuma

  DOI：10.1016/s0008-6215(00)81038-1

  日期：——

  -isopropylidene group, gave the corresponding 3- O -benzoyl derivatives ( 4 , 5 , and 7 ). Hydrogenation of benzyl 2-acetamido-4,6-di- O -acetyl-2-deoxy-3- O -[ d -1-(methoxycarbonyl)ethyl]-α- d -glucopyranoside, followed by chlorination, gave a product that was treated with mercuric actate to yield 2-acetamido-1,4,6-tri- O -acetyl-2-deoxy-3- O -[ d -1-(methoxycarbonyl)ethyl]-β- d -glucopyranose ( 11 ). Treatment

  摘要苄基2-乙酰氨基-2-脱氧-4,6-O-异亚丙基-α-d-吡喃葡萄糖苷的苄基化，苄基2-脱氧-2-（dl -3-羟基十四烷酰氨基）-4,6-O-异亚丙基-α -d-吡喃葡萄糖苷和苄基2-脱氧-4,6-O-异亚丙基-2-十八烷酰基氨基-β-d-吡喃葡萄糖苷，随后水解4,6-O-异亚丙基，得到相应的3-O-苯甲酰基衍生物（4，5和7）。苄基2-乙酰氨基-4,6-二-O-乙酰基-2-脱氧-3-O- [d -1-（甲氧羰基）乙基]-α-d-吡喃葡萄糖苷的氢化反应，得到的产物为用乙酸汞处理了2-乙酰氨基-1,4,6-三-O-乙酰基-2-脱氧-3-O- [d -1-（甲氧基羰基）乙基]-β-d-吡喃葡萄糖（11） 。用氯化铁处理11，得到恶唑啉衍生物，其与4、5，和7得到（1→6）-β-连接的二糖衍生物13、15和17。通过4-O-乙酰化作用水解13、15和17衍生化合物中的甲酯基团，得到相应的游
• Synthesis of β-<scp>d</scp>-Gal<i>f</i>-(1−3)-<scp>d</scp>-GlcNAc by the Trichloroacetamidate Method and of β-<scp>d</scp>-Gal<i>f</i>-(1−6)-<scp>d</scp>-GlcNAc by SnCl₄-Promoted Glycosylation
  作者：Carola Gallo-Rodriguez、Lucia Gandolfi、Rosa M. de Lederkremer

  DOI：10.1021/ol9905811

  日期：1999.7.1

  In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. beta-D-Galf-(1-3)-D-GlcNAc (1) was prepared by employing the trichloroacetamidate procedure for the glycosylation step, The mild conditions of this reaction are appropriate for condensation of 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl trichloroacetamidate (6) with acid-labile benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside (3). On the other hand, tin(IV) chloride promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (11) with penta-O-benzoyl-alpha,beta-D-galactofuranose (4) gave the derivative of beta-D-Galf-(1-6)-D-GlcNAc (2) in 78% yield.
• Synthesis of 4-acetamido-N-acetyl-4-deoxy- and 4,6-di(acetamido)-N-acetyl-4,6-dideoxy-muramoyl-l-alanyl-d-isoglutamine derivatives
  作者：Akira Hasegawa、Eiji Tanahashi、Yasuhiko Goh、Makoto Kiso

  DOI：10.1016/s0008-6215(00)80689-8

  日期：1982.5