(1R,2R,3S,4R,5R,6R)-5-hydroxymethyl-6-methanesulfonyloxycyclohexane-1,2,3,4-tetraol | 134651-20-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (1R,2R,3S,4R,5R,6R)-5-hydroxymethyl-6-methanesulfonyloxycyclohexane-1,2,3,4-tetraol
• 英文别名: [(1R,2R,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl] methanesulfonate
• CAS: 134651-20-0；136892-49-4；139402-99-6
• 化学式: C₈H₁₆O₈S
• 分子量: 272.276
• InChiKey: ZFQUAOYIVZOAJE-YAQXLYFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  153
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4R,5R,6R)-5-hydroxymethyl-6-methanesulfonyloxycyclohexane-1,2,3,4-tetraol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到(1R,2R,3S,4R,5R,6S)-5-hydroxymethyl-7-oxabicyclo<4.1.0>heptane-2,3,4-triol
  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：

  1D-4,5,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-chiro-inositol 在 palladium on activated charcoal 吡啶 、 咪唑 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 (1R,2R,3S,4R,5R,6R)-5-hydroxymethyl-6-methanesulfonyloxycyclohexane-1,2,3,4-tetraol
  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

文献信息

• A Divergent Route for a Total Synthesis of Cyclophellitol and Epicyclophellitol from a [2.2.2]Oxabicyclic Glycoside Prepared from D-Glucal
  作者：R. E. McDevitt、B Fraser-Reid

  DOI：10.1021/jo00091a004

  日期：1994.6

  D-Glucal has been used for syntheses of Tatsuta's penultimate intermediate for cyclophellitol and epicyclophellitol via a 6-exo-trig radical cyclization of 2-deoxy-2-iodo-6-alkynyl glycoside, the diastereomeric mixture produced thereby being separated into two sets, each of which leads to one or other target materials.