B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio- | 87470-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-
• 英文别名: S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-β-D-glucopyranoside；S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-α-D-glucopyranoside
• CAS: 87470-70-0；87470-72-2；129171-17-1；144830-21-7
• 化学式: C₃₃H₃₂O₅S
• 分子量: 540.68
• InChiKey: KDTRYCJSIFGZHI-QUEOJAHFSA-N

物化性质

• 沸点：
  675.3±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio- 在 Oxone 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-α-D-glucopyranoside sulfoxide
  参考文献：
  名称：

  Chemistry of 4,6-O-Benzylidene-d-glycopyranosyl Triflates:  Contrasting Behavior between the Gluco and Manno Series

  摘要：

  Activation of either anomer of S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-D-glucopyranoside with triflic anhydride in dichloromethane at -78 degrees C in the presence of 2,6-di-tert-butyl-4-methylpyridine affords a highly active glycosylating species which, on addition of alcohols, provides cl-glucosides with high selectivity. This selectivity stands in stark contrast to the analogous mannopyranoside series, which affords the beta-mannosides with excellent selectivity under the same conditions. Low-temperature NMR experiments support the notion that a glucosyl triflate is formed in the initial activation step. Possible reasons for the diverging stereoselectivity in the gluco and manno series are discussed.

  DOI：

  10.1021/jo990243d
• 作为产物：
  描述：

  phenyl 1-thio-D-glucopyranoside 在 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-
  参考文献：
  名称：

  Chemistry of 4,6-O-Benzylidene-d-glycopyranosyl Triflates:  Contrasting Behavior between the Gluco and Manno Series

  摘要：

  Activation of either anomer of S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-D-glucopyranoside with triflic anhydride in dichloromethane at -78 degrees C in the presence of 2,6-di-tert-butyl-4-methylpyridine affords a highly active glycosylating species which, on addition of alcohols, provides cl-glucosides with high selectivity. This selectivity stands in stark contrast to the analogous mannopyranoside series, which affords the beta-mannosides with excellent selectivity under the same conditions. Low-temperature NMR experiments support the notion that a glucosyl triflate is formed in the initial activation step. Possible reasons for the diverging stereoselectivity in the gluco and manno series are discussed.

  DOI：

  10.1021/jo990243d

文献信息

• Synthesis and Reactivity of 4′-Deoxypentenosyl Disaccharides
  作者：Panuwat Padungros、Ren-Hua Fan、Matthew D. Casselman、Gang Cheng、Hari R. Khatri、Alexander Wei

  DOI：10.1021/jo500449h

  日期：2014.6.6

  BSP/Tf2O activation, whereas β-linked 4′-DP disaccharides were generated by the decarboxylative elimination of glucuronyl disaccharides under microwave conditions. Both α- and β-linked 4′-DP disaccharides could be epoxidized with high stereoselectivity using DMDO. In some cases, the α-epoxypentenosides could be successfully converted into terminal l-iduronic acids via the syn addition of 2-furylzinc bromide

  4-脱氧戊烯苷 (4-DP) 是稀有或高级吡喃糖苷的通用合成子，它们为 C5 位置的结构多样化提供了一个入口。先前的研究表明，4-DPs 经历了立体控制的 DMDO 氧化；随后与各种亲核试剂的环氧化物开环可以以反或顺选择性进行。在这里，我们报告了 α-和 β-连接的 4'-脱氧戊烯糖 (4'-DP) 二糖的合成，并使用 DMDO 氧化/开环序列研究了它们的糖基化后 C5' 添加。α-连接的 4'-DP 二糖是通过使用 BSP/Tf 2将噻吩 4-DP 供体与糖基受体偶联来合成的O 活化，而 β-连接的 4'-DP 二糖是通过在微波条件下脱羧消除葡萄糖醛酸二糖而产生的。α-和β-连接的 4'-DP 二糖都可以使用 DMDO 以高立体选择性环氧化。在某些情况下，α-环氧戊烯苷可以通过2-呋喃基溴化锌的顺式加成成功转化为末端l-艾杜糖醛酸。这些研究支持了一种新的寡糖合成方法，其中末端 4'-DP
• Practical synthesis of oligosaccharides. Partial synthesis of avermectin B1a
  作者：K. C. Nicolaou、R. E. Dolle、D. P. Papahatjis

  DOI：10.1021/ja00327a021

  日期：1984.7