(2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal | 139285-93-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal
• CAS: 139285-93-1
• 化学式: C₂₈H₃₀O₅
• 分子量: 446.543
• InChiKey: GNXDWVUZHZXHBN-WXIAYYLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  33.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal 在 Raney-Ni-W₄ 吡啶 、 sodium hypochlorite 、 盐酸肼 、 dimethyl sulfide borane 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 56.0h， 生成 1D-4,5,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-chiro-inositol
  参考文献：
  名称：

  Total syntheses of glucosidase inhibitors, cyclophellitols

  摘要：

  A beta-D-glucosidase inhibitor, cyclophellitol [(1S,2R,3S,4R,5R,6R)-5-hydroxymethyl-7-oxabicyclo[4.1.0]heptane-2,3,4-triol, 1] and its epoxide diastereomer, 1,6-epicyclophellitol (2) have been synthesized by using an intramolecular [3 + 2]-cycloaddition of a nitrile oxide to an alkene as a key step. 2.3,4-Tri-O-benzyl-6,7-dideoxy-D-ido-hept-6-enose (E,Z)-oxime (6) was prepared from L-glucose in 11 steps. Intramolecular cycloaddition of 6 was realized by NaOCl via an intermediary nitrile oxide to afford the isoxazoline, (1S,2R,3S,4S,5R)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo[4.3.0]non-6-enc (7). Hydrogenolysis of 7 followed by a 5-step sequence gave cyclophellitol (1). Compound 2 was synthesized from methyl alpha-D-galactopyranoside by using a conceptually similar route. The glycosidase-inhibiting activities of 2 were examined.

  DOI：

  10.1016/0008-6215(91)89017-a
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 在 草酰氯 、 硫酸 、 sodium methylate 、 乙酸酐 、 二甲基亚砜 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.5h， 生成 (2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal
  参考文献：
  名称：

  Total syntheses of glucosidase inhibitors, cyclophellitols

  摘要：

  A beta-D-glucosidase inhibitor, cyclophellitol [(1S,2R,3S,4R,5R,6R)-5-hydroxymethyl-7-oxabicyclo[4.1.0]heptane-2,3,4-triol, 1] and its epoxide diastereomer, 1,6-epicyclophellitol (2) have been synthesized by using an intramolecular [3 + 2]-cycloaddition of a nitrile oxide to an alkene as a key step. 2.3,4-Tri-O-benzyl-6,7-dideoxy-D-ido-hept-6-enose (E,Z)-oxime (6) was prepared from L-glucose in 11 steps. Intramolecular cycloaddition of 6 was realized by NaOCl via an intermediary nitrile oxide to afford the isoxazoline, (1S,2R,3S,4S,5R)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo[4.3.0]non-6-enc (7). Hydrogenolysis of 7 followed by a 5-step sequence gave cyclophellitol (1). Compound 2 was synthesized from methyl alpha-D-galactopyranoside by using a conceptually similar route. The glycosidase-inhibiting activities of 2 were examined.

  DOI：

  10.1016/0008-6215(91)89017-a