Phenyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside | 244286-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: phenyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside；phenyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside；(2R,4aR,6R,7R,8S,8aR)-6-[(2R,3R,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 244286-77-9
• 化学式: C₆₀H₆₀O₁₀S
• 分子量: 973.196
• InChiKey: KJNNFKFEQGMWGZ-JEYYOWLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  71
• 可旋转键数：
  21
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Phenyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到phenyl 2,3,6,2',3',4'-hexa-O-benzyl-1-thio-β-D-maltoside
  参考文献：
  名称：

  Pearce, Alan James; Sollogoub, Matthieu; Mallet, Jean-Maurice, European Journal of Organic Chemistry, 1999, # 9, p. 2103 - 2117

  摘要：

  DOI：
• 作为产物：
  描述：

  phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside 在 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、133.32 Pa 条件下， 反应 2.0h， 生成 Phenyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Pearce, Alan James; Sollogoub, Matthieu; Mallet, Jean-Maurice, European Journal of Organic Chemistry, 1999, # 9, p. 2103 - 2117

  摘要：

  DOI：

文献信息

• New Phenyl 6,4′-Substituted-1-Thio-β-Maltosides, Building Blocks for The Synthesis of Linear and Branched Malto-oligosaccharides
  作者：Mohammed Saddik Motawia、Kim Larsen、Carl Erik Olsen、Birger Lindberg Møller

  DOI：10.1055/s-2000-7601

  日期：——

  An efficient strategy to synthesize a number of new phenylthio-maltoside derivatives in yields from 55 to 95% is described. These derivatives can be used as suitable building blocks for stepwise synthesis of starch derived malto-oligosaccharides.

  描述了一种高效的策略，可以合成多种新的苯硫苷麦芽糖衍生物，其产率在55%到95%之间。这些衍生物可以作为分步合成淀粉衍生麦芽寡糖的合适构件。
• A metal free mild and green approach for tandem opening of 4,6-O-benzylidene acetals to their corresponding 6-O-acetyl derivatives: Application in the synthesis of a trisaccharide using one-pot glycosylation reactions
  作者：Mana Mohan Mukherjee、Nabamita Basu、Shantanu Nandi、Rina Ghosh

  DOI：10.1016/j.carres.2019.03.002

  日期：2019.4

  An efficient and high yielding reaction for tandem opening of 4,6-O-benzylidene derivatives (gluco, galacto, manno, 2-phthalimido-2-deoxy glucosides) to their corresponding 6-O-acetyl derivatives has been established under metal free condition using 60% solution of aqueous acetic acid (v/v). The reaction is equally pertinent for large scale synthesis and also for disaccharide glycosides. Its application

  在无金属条件下，已经建立了一种高效，高产率的串联打开4,6-O-亚苄基衍生物（葡萄糖，半乳糖，甘露糖，2-邻苯二甲酰亚胺基-2-脱氧葡萄糖苷）为其相应的6-O-乙酰基衍生物的反应。使用60％的醋酸水溶液（v / v）。该反应对于大规模合成以及对二糖苷而言同样重要。还已经描述了其在构建用于利用一锅糖基化反应合成与铜绿假单胞菌有关的三糖部分的结构单元中的应用。
• Pearce, Alan James; Sollogoub, Matthieu; Mallet, Jean-Maurice, European Journal of Organic Chemistry, 1999, # 9, p. 2103 - 2117
  作者：Pearce, Alan James、Sollogoub, Matthieu、Mallet, Jean-Maurice、Sinay, Pierre

  DOI：——

  日期：——
• DISAL Glycosyl Donors for the Synthesis of a Linear Hexasaccharide under Mild Conditions
  作者：Lars Petersen、Jane B. Laursen、Kim Larsen、M. Saddik Motawia、Knud J. Jensen

  DOI：10.1021/ol034242q

  日期：2003.4.1

  The new class of glycosyl donors with a methyl 3,5-dinitrosalicylate (DISAL) anomeric leaving group has proved efficient for glycosylation under strictly neutral, mildly basic, or mildly acidic conditions. Here, we report the synthesis of novel DISAL disaccharide glycosyl donors prepared by easy nucleophilic aromatic substitution. These DISAL donors proved efficient in the synthesis of a starch-related hexasaccharide under very mild conditions. Glycosylations proceeded with alpha-selectivity and were compatible with Trt protecting groups.