phenyl(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-glucopyranoside) | 225242-73-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-glucopyranoside)
• 英文别名: (2R,3S,4R,5R,6S)-2-(Acetoxymethyl)-6-(phenylthio)-5-(2,2,2-trifluoroacetamido)tetrahydro-2H-pyran-3,4-diyl diacetate；[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-phenylsulfanyl-5-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 225242-73-9
• 化学式: C₂₀H₂₂F₃NO₈S
• 分子量: 493.458
• InChiKey: BCUSMKIGPDPBIG-ZKXLYKBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  phenyl(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-glucopyranoside) 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-(benzenesulfinyl)-5-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Stereospecific Solution- and Solid-Phase Glycosylations. Synthesis of β-Linked Saccharides and Construction of Disaccharide Libraries Using Phenylsulfenyl 2-Deoxy-2-Trifluoroacetamido Glycopyranosides as Glycosyl Donors¹

  摘要：

  An efficient strategy to construct beta-O-2-amino-2-deoxyglycopyranosidic linkages using glycosyl sulfoxides is demonstrated. Phenylsulfenyl 2-deoxy-2-trifluoroacetamido glycopyranosides were found to be reactive glycosyl donors in both solid- and solution-phase glycosylations, affording the corresponding beta-glycosides exclusively and in high yield. The trifluoroacetamido group was removed under mild conditions, allowing orthogonal derivatization of multiple protected amino groups on an oligosaccharide or glycoconjugate. On the basis of the results with these glycosyl donors, a solid-phase beta-linked disaccharide library was constructed. The scope and flexibility of this approach will be discussed.

  DOI：

  10.1021/jo9903499
• 作为产物：
  描述：

  2-deoxy-2-[p-methoxybenzylidene(amino)]-β-D-glucopyranose 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 phenyl(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-glucopyranoside)
  参考文献：
  名称：

  Stereospecific Solution- and Solid-Phase Glycosylations. Synthesis of β-Linked Saccharides and Construction of Disaccharide Libraries Using Phenylsulfenyl 2-Deoxy-2-Trifluoroacetamido Glycopyranosides as Glycosyl Donors¹

  摘要：

  An efficient strategy to construct beta-O-2-amino-2-deoxyglycopyranosidic linkages using glycosyl sulfoxides is demonstrated. Phenylsulfenyl 2-deoxy-2-trifluoroacetamido glycopyranosides were found to be reactive glycosyl donors in both solid- and solution-phase glycosylations, affording the corresponding beta-glycosides exclusively and in high yield. The trifluoroacetamido group was removed under mild conditions, allowing orthogonal derivatization of multiple protected amino groups on an oligosaccharide or glycoconjugate. On the basis of the results with these glycosyl donors, a solid-phase beta-linked disaccharide library was constructed. The scope and flexibility of this approach will be discussed.

  DOI：

  10.1021/jo9903499

文献信息

• An expeditious and efficient synthesis of β-d-galactopyranosyl-(1→3)-d-N-acetylglucosamine (lacto-N-biose) using a glycosynthase from Thermus thermophilus as a catalyst
  作者：Ayité D’Almeida、Marina Ionata、Vinh Tran、Charles Tellier、Michel Dion、Claude Rabiller

  DOI：10.1016/j.tetasy.2009.05.007

  日期：2009.6

  Mutant glycosynthases or transglycosidases obtained from a Thermus thermophilus β-d-glycosidase (TtbGly) efficiently catalyzed the synthesis of β-(1→3)-disaccharides. Unfortunately, this regioselectivity was changed to the β-(1→4) one when N-acetylglucosamine derivatives were used as acceptors, thus precluding the possibility of synthesizing d-Galp-β-(1→3)-d-GlcpNAc (lacto-N-biose) or d-Glcp-β-(1→3)-d-GlcpNAc

  从嗜热栖热菌β-d-糖苷酶（TtbGly）获得的突变糖合酶或转糖苷酶有效地催化了β-（1→3）-二糖的合成。不幸的是，当使用N-乙酰基葡糖胺衍生物作为受体时，该区域选择性变成了β-（1→4），因此排除了合成d-Gal p - β-（1→3）-d-Glc p NAc的可能性。（乳糖-N-二糖）或d-Glc p - β-（1→3）-d-Glc pNAc，是合成抗原决定簇的有用合成子。相反，我们在这项工作中表明，在存在苯基2-氨基-1-硫代-β-d-吡喃葡萄糖苷的情况下，发生了E338G TtbGly糖合酶的“正常”β-（1→3）区域选择性。因此，使用α-半乳糖基或α-葡萄糖基氟化物进行转糖基化反应可得到高收率的相应苯基β-d-glycopyranosyl-（1→3）-2-氨基-2-脱氧-1-硫代-β-d-葡萄糖基吡喃糖苷（88 –97％）。随后的选择性N-酰化，然后对苯硫醚进行NBS /水脱保
• WO2008/153394
  申请人：——

  公开号：——

  公开（公告）日：——