(5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol | 141458-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol
• 英文别名: (2S,5S,6R)-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-ol
• CAS: 141458-83-5
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: ABQHWJWYOSYEHM-ZCNNSNEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 生成 4,6-di-O-benzyl-2,3-dideoxy-D-gluconolactone
  参考文献：
  名称：

  A General Method for Convergent Synthesis of Polycyclic Ethers Based on Suzuki Cross-Coupling:  Concise Synthesis of the ABCD Ring System of Ciguatoxin

  摘要：

  [GRAPHICS]A general method for convergent assembly of polyether structure has been developed based on palladium(0)-mediated Suzuki cross-coupling reaction of alkylboranes with cyclic ketene acetal phosphates. The present method allowed for coupling of medium-sited ether rings and thus a concise synthesis of the ABCD ring system of ciguatoxins has been achieved.

  DOI：

  10.1021/ol990885n
• 作为产物：
  描述：

  t-butyl 2,3-dideoxy-α-D-gluco-pyranoside 在 盐酸 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol
  参考文献：
  名称：

  A General Method for Convergent Synthesis of Polycyclic Ethers Based on Suzuki Cross-Coupling:  Concise Synthesis of the ABCD Ring System of Ciguatoxin

  摘要：

  [GRAPHICS]A general method for convergent assembly of polyether structure has been developed based on palladium(0)-mediated Suzuki cross-coupling reaction of alkylboranes with cyclic ketene acetal phosphates. The present method allowed for coupling of medium-sited ether rings and thus a concise synthesis of the ABCD ring system of ciguatoxins has been achieved.

  DOI：

  10.1021/ol990885n

文献信息

• Regioselective Anomeric <i>O</i> ‐Benzyl Deprotection in Carbohydrates
  作者：Perali Ramu Sridhar、Bandi Anjaneyulu、Boddu Umamaheswara Rao

  DOI：10.1002/ejoc.202101033

  日期：2021.11.8

  A simple and highly regioselective hydrogenolysis of the anomeric benzyl group is reported. The generality and the scope of the reaction were evaluated by applying it to a number of diversly protected benzyl monosaccharides and disaccharides that lead to the formation of the corresponding hemiacetals in good yield.

  报道了异头苄基的简单且高度区域选择性的氢解。反应的一般性和范围是通过将其应用于许多不同保护的苄基单糖和二糖来评估的，这些苄基单糖和二糖导致以良好的产率形成相应的半缩醛。
• A General Method for Convergent Synthesis of Polycyclic Ethers Based on Suzuki Cross-Coupling:  Concise Synthesis of the ABCD Ring System of Ciguatoxin
  作者：Makoto Sasaki、Haruhiko Fuwa、Makoto Ishikawa、Kazuo Tachibana

  DOI：10.1021/ol990885n

  日期：1999.10.1

  [GRAPHICS]A general method for convergent assembly of polyether structure has been developed based on palladium(0)-mediated Suzuki cross-coupling reaction of alkylboranes with cyclic ketene acetal phosphates. The present method allowed for coupling of medium-sited ether rings and thus a concise synthesis of the ABCD ring system of ciguatoxins has been achieved.