(2R,3R,4R,5R,6R)-2,3,6-trimethoxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-4-ol | 1044736-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6R)-2,3,6-trimethoxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-4-ol
• CAS: 1044736-05-1
• 化学式: C₂₃H₃₀O₇
• 分子量: 418.487
• InChiKey: VASHQKPSJZLEPW-GNJRFXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6R)-2,3,6-trimethoxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-4-ol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 以84%的产率得到(2R,3R,4S,5R,6R)-2,3,6-trimethoxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-4-ol
  参考文献：
  名称：

  A new stereoselective approach to a selectively protected derivative of d-pinitol and its evaluation as α-l-rhamnopyranose mimetic

  摘要：

  The synthesis of 3,5-di-O-benzyl-D-pinitol has been stereoselectively accomplished through intramolecular aldolization of 2,6-di-O-benzyl-4-O-methyl-L-lyxo-hexos-5-ulose followed by reduction with NaBH(OAc)(3). Computational analysis [DFT calculations at the B3LYP/6-31G(d) level] suggests that D-pinitol in water largely prefers the conformation corresponding to the (1)C4 one of a alpha-L-rhamnopyranoside unit, being thus a good candidate for its mimicking. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.040
• 作为产物：
  描述：

  methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranoside 、 碘甲烷 在 四丁基溴化铵 、 二正丁基氧化锡 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 、 N,N-二甲基甲酰胺 、 水 、 乙腈 为溶剂， 以88%的产率得到(2R,3R,4R,5R,6R)-2,3,6-trimethoxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-4-ol
  参考文献：
  名称：

  A new stereoselective approach to a selectively protected derivative of d-pinitol and its evaluation as α-l-rhamnopyranose mimetic

  摘要：

  The synthesis of 3,5-di-O-benzyl-D-pinitol has been stereoselectively accomplished through intramolecular aldolization of 2,6-di-O-benzyl-4-O-methyl-L-lyxo-hexos-5-ulose followed by reduction with NaBH(OAc)(3). Computational analysis [DFT calculations at the B3LYP/6-31G(d) level] suggests that D-pinitol in water largely prefers the conformation corresponding to the (1)C4 one of a alpha-L-rhamnopyranoside unit, being thus a good candidate for its mimicking. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.040

文献信息

• A new stereoselective approach to a selectively protected derivative of d-pinitol and its evaluation as α-l-rhamnopyranose mimetic
  作者：Giorgio Catelani、Felicia D’Andrea、Alessio Griselli、Lorenzo Guazzelli、Laura Legnani、Lucio Toma

  DOI：10.1016/j.tetlet.2008.05.040

  日期：2008.7

  The synthesis of 3,5-di-O-benzyl-D-pinitol has been stereoselectively accomplished through intramolecular aldolization of 2,6-di-O-benzyl-4-O-methyl-L-lyxo-hexos-5-ulose followed by reduction with NaBH(OAc)(3). Computational analysis [DFT calculations at the B3LYP/6-31G(d) level] suggests that D-pinitol in water largely prefers the conformation corresponding to the (1)C4 one of a alpha-L-rhamnopyranoside unit, being thus a good candidate for its mimicking. (c) 2008 Elsevier Ltd. All rights reserved.