benzyl (phenyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-1-thio-β-D-glucopyranoside)uronate | 1607445-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (phenyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-1-thio-β-D-glucopyranoside)uronate
• CAS: 1607445-15-7
• 化学式: C₃₄H₄₂O₆SSi
• 分子量: 606.855
• InChiKey: NKAIKNDBPCWVOG-PJRGDJDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.66
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside 、 benzyl (phenyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-1-thio-β-D-glucopyranoside)uronate 在 二苯基甲烷硫酮 、 2,4,6-三叔丁基嘧啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.49h， 以67%的产率得到ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of benzyl protected β-d-GlcA-(1→2)-α-d-Man thioglycoside building blocks for construction of Cryptococcus neoformans capsular polysaccharide structures

  摘要：

  In a project targeting the synthesis of large oligosaccharide structures corresponding to the Cryptococcus neoformans GXM capsular polysaccharide, an easy access to thiodisaccharide building blocks comprising a beta-linked glucuronic acid moiety and a 6-O-acetyl group was required. Several pathways to such building blocks have been investigated, addressing the problem of constructing a beta-linked glucuronic acid residue protected with groups that are orthogonal to a primary acetyl group. Two efficient routes have been developed, one using benzoylated glucosyl donors to form the beta-linkage followed by a change of protecting groups to benzyls and subsequent introduction of the carboxyl function and the acetyl group. The second route explored the possibility to achieve beta-selectivity using glucuronyl donors without acyl protecting groups. BF3- etherate promoted glycosylations with benzyl (2,3,4-tri-O-benzyl-alpha-D-glucupyranosyl)uronate trichloroacetimidate in the presence of nitrile solvents and at low temperatures reproducibly gave good yields of disaccharides with high beta-selectivity. Furthermore, the use of recently reported glucuronyl thioglycoside donors protected with a cyclic 2,4-silylene acetal was found to represent another efficient and completely beta-selective way to desired disaccharide building blocks. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.01.022
• 作为产物：
  描述：

  phenyl 3-O-benzyl-1-thio-β-D-glucopyranoside 在 2,6-二甲基吡啶 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 caesium carbonate 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 benzyl (phenyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-1-thio-β-D-glucopyranoside)uronate
  参考文献：
  名称：

  Synthesis of benzyl protected β-d-GlcA-(1→2)-α-d-Man thioglycoside building blocks for construction of Cryptococcus neoformans capsular polysaccharide structures

  摘要：

  In a project targeting the synthesis of large oligosaccharide structures corresponding to the Cryptococcus neoformans GXM capsular polysaccharide, an easy access to thiodisaccharide building blocks comprising a beta-linked glucuronic acid moiety and a 6-O-acetyl group was required. Several pathways to such building blocks have been investigated, addressing the problem of constructing a beta-linked glucuronic acid residue protected with groups that are orthogonal to a primary acetyl group. Two efficient routes have been developed, one using benzoylated glucosyl donors to form the beta-linkage followed by a change of protecting groups to benzyls and subsequent introduction of the carboxyl function and the acetyl group. The second route explored the possibility to achieve beta-selectivity using glucuronyl donors without acyl protecting groups. BF3- etherate promoted glycosylations with benzyl (2,3,4-tri-O-benzyl-alpha-D-glucupyranosyl)uronate trichloroacetimidate in the presence of nitrile solvents and at low temperatures reproducibly gave good yields of disaccharides with high beta-selectivity. Furthermore, the use of recently reported glucuronyl thioglycoside donors protected with a cyclic 2,4-silylene acetal was found to represent another efficient and completely beta-selective way to desired disaccharide building blocks. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.01.022