benzyl (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)carbamate | 516482-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)carbamate
• 英文别名: N-benzyloxycarbonyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranosylamine；N-benzyloxycarbonyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine；benzyl N-[(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]carbamate
• CAS: 516482-65-8
• 化学式: C₄₂H₄₃NO₇
• 分子量: 673.806
• InChiKey: ZUWRNCYWHCLKQL-WWGFXPMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 benzyl (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)carbamate 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 benzyl [(2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-1-(2-oxo-2-phenylethyl)hexyl]carbamate
  参考文献：
  名称：

  路易斯酸催化糖衍生半环 N,O-缩醛的开环反应

  摘要：

  N-(烷氧基羰基)-N-糖苷(聚氧半环N,O-缩醛) 由常规乙酰基或甲基糖苷(吡喃葡萄糖苷、呋喃核糖苷、阿拉伯呋喃糖苷和2-脱氧呋喃核糖苷) 和氨基甲酸酯通过三甲基甲硅烷基三氟甲磺酸酯和4 A 处理有效合成分子筛。发现这些N-糖苷与硅烷化亲核试剂发生路易斯酸催化的开环反应，得到具有良好至高非对映选择性的开环氨基醇。揭示了反应性顺序，2-脱氧呋喃糖苷 > 阿拉伯呋喃糖苷 > 呋喃糖苷 > 吡喃葡萄糖苷。还用硅烷或氢化二异丁基铝研究了开环还原。发现合适的还原剂取决于所使用的 N-糖苷。糖苷酶抑制剂，（2S，3R，

  DOI：

  10.1002/1522-2675(200211)85:11<3678::aid-hlca3678>3.0.co;2-0
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 、 氨基甲酸苄酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到benzyl (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)carbamate
  参考文献：
  名称：

  Synthesis of new β-1-C-alkylated imino-l-iditols: A comparative study of their activity as β-glucocerebrosidase inhibitors

  摘要：

  A short synthesis of new beta-1-C-alkyl-1,5-dideoxy-1,5-imino-L-iditols by means of the diastereoselective addition of Grignard reagents onto a glucopyranosylamine is described. These compounds were evaluated as beta-glucocerebrosidase inhibitors and their activity was compared with that of related iminosugar derivatives in the D-gluco and D-xylo series. The results allowed us to conclude on the influence of the hydroxymethyl moiety and of the piperidine-ring conformation on the inhibitory activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.027

文献信息

• One-step synthesis of N-protected glycosylamines from sugar hemiacetals
  作者：Virginie Liautard、Christelle Pillard、Valérie Desvergnes、Olivier R. Martin

  DOI：10.1016/j.carres.2007.11.022

  日期：2008.8

  Protected pentofuranose, hexofuranose and hexopyranose hemiacetals were found to react efficiently with amines carrying a deactivating group (alkoxycarbonyl, tosyl or phosphoryl group) in the presence of a Lewis acid to give the corresponding, stable glycosylamines. Such glycosylamine derivatives are useful substrates for further elaboration into nitrogen-containing natural products and carbohydrate mimetics. (C) 2007 Elsevier Ltd. All rights reserved.
• Lewis Acid Catalyzed Ring-Opening Reactions of Sugar-Derived Semicyclic N,O-Acetals
  作者：Masaharu Sugiura、Hiroyuki Hagio、Shu Kobayashi

  DOI：10.1002/1522-2675(200211)85:11<3678::aid-hlca3678>3.0.co;2-0

  日期：2002.11

  efficiently synthesized from regular acetyl or methyl glycosides (glucopyranoside, ribofuranoside, arabinofuranoside, and 2-deoxyribofuranoside) and a carbamate by treatment of trimethylsilyl trifluoromethanesulfonate and 4 A molecular sieves. It was found that these N-glycosides underwent Lewis acid catalyzed ring-opening reactions with silylated nucleophiles to give ring-opened amino alcohols with good-to-high

  N-(烷氧基羰基)-N-糖苷(聚氧半环N,O-缩醛) 由常规乙酰基或甲基糖苷(吡喃葡萄糖苷、呋喃核糖苷、阿拉伯呋喃糖苷和2-脱氧呋喃核糖苷) 和氨基甲酸酯通过三甲基甲硅烷基三氟甲磺酸酯和4 A 处理有效合成分子筛。发现这些N-糖苷与硅烷化亲核试剂发生路易斯酸催化的开环反应，得到具有良好至高非对映选择性的开环氨基醇。揭示了反应性顺序，2-脱氧呋喃糖苷 > 阿拉伯呋喃糖苷 > 呋喃糖苷 > 吡喃葡萄糖苷。还用硅烷或氢化二异丁基铝研究了开环还原。发现合适的还原剂取决于所使用的 N-糖苷。糖苷酶抑制剂，（2S，3R，
• Synthesis of new β-1-C-alkylated imino-l-iditols: A comparative study of their activity as β-glucocerebrosidase inhibitors
  作者：Wojciech Schönemann、Estelle Gallienne、Philippe Compain、Kyoko Ikeda、Naoki Asano、Olivier R. Martin

  DOI：10.1016/j.bmc.2010.02.027

  日期：2010.4

  A short synthesis of new beta-1-C-alkyl-1,5-dideoxy-1,5-imino-L-iditols by means of the diastereoselective addition of Grignard reagents onto a glucopyranosylamine is described. These compounds were evaluated as beta-glucocerebrosidase inhibitors and their activity was compared with that of related iminosugar derivatives in the D-gluco and D-xylo series. The results allowed us to conclude on the influence of the hydroxymethyl moiety and of the piperidine-ring conformation on the inhibitory activity. (C) 2010 Elsevier Ltd. All rights reserved.