phthalimidyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside | 116417-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phthalimidyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside
• 英文别名: 2-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyisoindole-1,3-dione
• CAS: 116417-79-9
• 化学式: C₄₂H₃₉NO₈
• 分子量: 685.774
• InChiKey: JRWZXQGTIVZLTM-QBRMMRRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phthalimidyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 1.0h， 生成 2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyisoindole-1,3-dione
  参考文献：
  名称：

  Expedient synthesis of aminooxylated-carbohydrates for chemoselective access of glycoconjugates

  摘要：

  Herein, we describe an efficient preparation of various biologically important carbohydrate motifs bearing an aminooxy group at the anomeric position. These nucleophilic sugar analogues represent useful intermediates for the chemoselective preparation of glycoconjugates. The key glycosylation step involves the coupling of fluoro-activated protected sugar and N-hydroxyphthalimide in the presence of BF3. Et2O. Final deprotection and cleavage of the phthalimide moiety with methylhydrazine afforded new Glc-beta -ONH2 3, GalNAc-beta -ONH2 9, Glc-alpha -ONH2 14, Gal-alpha -ONH2 17 and Man-alpha -ONH2 20 derivatives with good yields. Compared to the literature results, the preparation of Gal-beta -ONH2 6, GalNAc-alpha -ONH2 11 and Lac-beta -ONH2 23 proved to be more efficient. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01614-8
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 2,3,4,6-四苄基-D-吡喃葡萄糖 生成 phthalimidyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside
  参考文献：
  名称：

  GROCHOWSKI, EDWARD;NASHED, EUGENIA M.;JURCZAK, JANUSZ, BULL. POL. ACAD. SCI. CHEM., 35,(1987) N 7-8, 255-260

  摘要：

  DOI：

文献信息

• <i>O</i>-Glycosylation Enabled by <i>N-</i>(Glycosyloxy)acetamides
  作者：Miao Liu、Bo-Han Li、De-Cai Xiong、Xin-Shan Ye

  DOI：10.1021/acs.joc.8b01003

  日期：2018.8.3

  A novel glycosylation protocol has been established by using N-(glycosyloxy)acetamides as glycosyl donors. The N-oxyacetamide leaving group in donors could be rapidly activated in the presence of Cu(OTf)2 or SnCl4 under microwave irradiation. This glycosylation process afforded the coupled products in high yields, and the reaction enjoyed a broad substrate scope, even for disarmed donors and hindered

  通过使用N-（糖基氧基）乙酰胺作为糖基供体已经建立了新的糖基化方案。在微波辐射下，存在Cu（OTf）2或SnCl 4的情况下，供体中的N-氧乙酰胺离去基团可以快速活化。该糖基化过程以高收率提供了偶联产物，并且该反应享有广泛的底物范围，即使对于缴械的供体和受阻的受体也是如此。供体的容易获得，N-（糖基氧基）乙酰胺的高稳定性以及小的离去基团使该方法非常实用。
• <i>C</i>-Glycosylation enabled by <i>N</i>-(glycosyloxy)acetamides
  作者：Miao Liu、Bo-Han Li、Tian Li、Xia Wu、Meng Liu、De-Cai Xiong、Xin-Shan Ye

  DOI：10.1039/d0ob00561d

  日期：——

  The C-glycosylation of C-nucleophiles including allyltrimethylsilane, silyl enol ethers and phenols with N-(glycosyloxy)acetamides as glycosyl donors has been realized. This protocol provides a convenient and practical route for the synthesis of alkyl C-glycosides and aryl 2-deoxy-β-C-glycosides under mild reaction conditions.

  已经实现了包含N-（糖基氧基）乙酰胺作为糖基供体的C-亲核试剂（包括烯丙基三甲基硅烷，甲硅烷基烯醇醚和苯酚）的C-糖基化。该方案为在温和的反应条件下合成烷基C-糖苷和芳基2-脱氧-β-C-糖苷提供了方便实用的途径。
• O-Glycosylhydroxylamines: A new class of monosaccharide
  作者：Eugenia M. Nashed、Edward Grochowski、Ewa Czyzewska

  DOI：10.1016/0008-6215(90)84118-e

  日期：1990.2

  Synthese d'acide N-acetyl O-[tetra-O-benzyl-2,3,4,6 hexopyranosyl] acetohydroxamique a partir d'O-phtalimido-1 tri-O-benzyl-2,3,5 ribofuranose, d'hydrazine et d'anhydride d'acide acetique

  合成d'acide N-乙酰基O- [四-O-苄基-2,3,4,6己吡喃糖基]乙酰氧肟酸d'O-邻苯二甲酰亚胺-1三-O-苄基-2,3,5呋喃核糖，d'肼及乙酸酐
• Grochowski, Edward; Nashed, Eugenia M.; Jurczak, Janusz, Bulletin of the Polish Academy of Sciences: Chemistry, 1987, vol. 35, # 7-8, p. 255 - 260
  作者：Grochowski, Edward、Nashed, Eugenia M.、Jurczak, Janusz

  DOI：——

  日期：——
• NASHED, EUGENIA M.;GROCHOWSKI, EDWARD;CZYZEWSKA, EWA, CARBOHYDR. RES., 196,(1990) C. 184-190
  作者：NASHED, EUGENIA M.、GROCHOWSKI, EDWARD、CZYZEWSKA, EWA

  DOI：——

  日期：——