Benzoic acid (2R,3S,4S,5S,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-hydroxy-tetrahydro-pyran-3-yl ester | 154920-23-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2R,3S,4S,5S,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-hydroxy-tetrahydro-pyran-3-yl ester
• 英文别名: Bz(-2)[Bn(-4)][TBDPS(-6)]Man(a)-SEt；[(2R,3S,4S,5S,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-ethylsulfanyl-4-hydroxy-5-phenylmethoxyoxan-3-yl] benzoate
• CAS: 154920-23-7
• 化学式: C₃₈H₄₄O₆SSi
• 分子量: 656.915
• InChiKey: VUULDRKOZMJYOV-BQAFVNTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3S,4S,5S,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-hydroxy-tetrahydro-pyran-3-yl ester 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以68%的产率得到ethyl 2-O-benzoyl-4-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  利用环己烷-1,2-二缩醛方法进行寡糖组装的新策略：高甘露糖型九糖的高效合成

  摘要：

  AbstractThe high‐mannose nonasaccharide 1 is part of the glycoprotein gp 120 of the viral coat of HIV‐1. The mannan portion of this triantennary glycan was prepared by a number of consecutive glycosidation steps without the need for any protecting‐group manipulation. This was achieved by carefully tuning the reactivity of the glycosyl donors by employing our cyclohexane‐1,2‐diacetal (CDA) methodology. The method was further extended with one‐pot procedures for oligosaccharide synthesis, thus reducing the number of steps to form the protected nonasaccharide 21 from the monosaccharide building blocks to five.

  DOI：

  10.1002/chem.19970030315
• 作为产物：
  描述：

  ethyl 1-thio-α-D-mannopyranoside 在 phase transfer 4-二甲氨基吡啶 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 Benzoic acid (2R,3S,4S,5S,6R)-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-4-hydroxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  合成中的双螺合酮（第5部分）：使用差异激活的糖基供体和受体进行寡糖合成的新机会

  摘要：

  双螺酮保护的硫糖苷的反应活性使其成为寡糖合成的有用的新前体，如制备布鲁氏锥虫变体表面糖蛋白共有的受保护的五糖单元所示。

  DOI：

  10.1016/s0040-4039(00)61375-8

文献信息

• Dispiroketals in synthesis (Part 5): A new opportunity for oligosaccharide synthesis using differentially activated glycosyl donors and acceptors
  作者：Geert-Jan Boons、Peter Grice、Ray Leslie、Steven V Ley、Lam Lung Yeung

  DOI：10.1016/s0040-4039(00)61375-8

  日期：1993.1

  The reactivity of dispiroketal protected thioglycosides makes them useful new precursors for oligossaccharide synthesis as is illustrated by the preparation of a protected pentasaccharide unit common to the variant surface glycoprotein of Trypanosoma brucei.

  双螺酮保护的硫糖苷的反应活性使其成为寡糖合成的有用的新前体，如制备布鲁氏锥虫变体表面糖蛋白共有的受保护的五糖单元所示。
• A New Strategy for Oligosaccharide Assembly Exploiting Cyclohexane-1,2-diacetal Methodology: An Efficient Synthesis of a High Mannose Type Nonasaccharide
  作者：Peter Grice、Steven V. Ley、Jörg Pietruszka、Helen M. I. Osborn、Henning W. M. Priepke、Stuart L. Warriner

  DOI：10.1002/chem.19970030315

  日期：——

  AbstractThe high‐mannose nonasaccharide 1 is part of the glycoprotein gp 120 of the viral coat of HIV‐1. The mannan portion of this triantennary glycan was prepared by a number of consecutive glycosidation steps without the need for any protecting‐group manipulation. This was achieved by carefully tuning the reactivity of the glycosyl donors by employing our cyclohexane‐1,2‐diacetal (CDA) methodology. The method was further extended with one‐pot procedures for oligosaccharide synthesis, thus reducing the number of steps to form the protected nonasaccharide 21 from the monosaccharide building blocks to five.