(1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate | 139402-99-6

• 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: (1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate
• 英文别名: [(1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl] methanesulfonate
• CAS: 139402-99-6
• 化学式: C₈H₁₆O₈S
• 分子量: 272.276
• InChiKey: ZFQUAOYIVZOAJE-CIAXFZGJSA-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：

  (1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate 在 sodium hydroxide 作用下， 反应 1.0h， 以82%的产率得到(1R,2R,3R,4S,5R,6S)-2-(羟基甲基)-7-氧杂双环[4.1.0]庚烷-3,4,5-三醇
  参考文献：
  名称：

  利用氯化钯介导的-Ferrier-II 重排合成环磷脂醇

  摘要：

  Cyclophellitol 及其 C3-差向异构体分别由 5-enoglucopyranoside 和 5-enomannopyranoside 合成。碳环骨架是通过 PdCl2 介导的 Ferrier-II 反应构建的。

  DOI：

  10.3390/10080901
• 作为产物：
  描述：

  (2S,3R,4S)-2,3,4-tris-benzyloxy-5-hydroxycyclohexan-1-one 在 palladium dihydroxide sodium tetrahydroborate 、 disodium hydrogenphosphate 、 cerium(III) chloride 、 氢气 、 sodium hydride 、 甲基磺酰氯 、 三乙胺 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 277.75h， 生成 (1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate
  参考文献：
  名称：

  利用氯化钯介导的-Ferrier-II 重排合成环磷脂醇

  摘要：

  Cyclophellitol 及其 C3-差向异构体分别由 5-enoglucopyranoside 和 5-enomannopyranoside 合成。碳环骨架是通过 PdCl2 介导的 Ferrier-II 反应构建的。

  DOI：

  10.3390/10080901

文献信息

• An efficient synthesis of cyclophellitol utilizing unusual regioselectivity of oxirane ring opening with Mes2BCH2Li
  作者：Hideyo Takahashi、Takamasa Iimori、Shiro Ikegami

  DOI：10.1016/s0040-4039(98)01458-0

  日期：1998.9

  Cyclophellitol has been synthesized from 5,6-enoglucoside efficiently. The carbacyclic skeleton was constructed through a Ferrier reaction mediated by PdCl2. The regioselectivity on the oxirane ring opening with Mes(2)BCH(2)Li at the key step is found to be controlled by the hydroxy protecting group. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Total syntheses of glucosidase inhibitors, cyclophellitols
  作者：Kuniaki Tatsuta、Yoshihisa Niwata、Kazuo Umezawa、Kazunobu Toshima、Masaya Nakata

  DOI：10.1016/0008-6215(91)89017-a

  日期：1991.12

  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.
• 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.