isobutyl DL-β-amicetoside | 75041-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: isobutyl DL-β-amicetoside
• 英文别名: (2S,3R,6S)-2-methyl-6-(2-methylpropoxy)oxan-3-ol
• CAS: 75041-68-8；75041-69-9；96292-26-1；96292-27-2；96292-28-3；96292-29-4；102850-47-5
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: DHMBVXMLFUTNNJ-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isobutyl DL-β-amicetoside 生成 (2R,3S,6R)-2-methyl-6-(2-methylpropoxy)oxan-3-ol
  参考文献：
  名称：

  Synthesis of amicetose by three enantioselective methods

  摘要：

  Three methods for the synthesis of the deoxy sugar amicetose (2,3,6-trideoxy-D-erythro-hexopyranoside) are described. All three utilize the known dihydropyran 2-isobutoxy-6-methyl-2,3-dihydro-4H-pyran as an intermediate. Asymmetric hydroboration of the dihydropyran with IpcBH(2) gave enantiomerically enriched isobutyl ex and beta-amicetosides. Hydroboration with borane-tetrahydrofuran followed by derivatization of the major product (beta-anomer) with R-(-)-1-(1-naphthyl)ethylisocyanate gave diastereomeric carbamates which were separated and converted to isobutyl beta-D and beta-L-amicetosides having high optical purity. Racemic isobutyl beta-amicetosides were also resolved by enzymatic transesterification using lipase and an acyl transfer reagent. Porcine pancreatic lipase and lipases from Candida rugosa and Pseudomonas sp. were evaluated in the presence of either vinyl acetate, vinyl butyrate, or trifluoroethyl butyrate as acylating agents. A GC-based method for determining enantiomeric purity of amicetose derivatives was developed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00631-9
• 作为产物：
  描述：

  乙烯基异丁醚 在 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 作用下， 以 正己烷 为溶剂， 反应 4.0h， 生成 isobutyl DL-β-amicetoside
  参考文献：
  名称：

  外消旋脱水脱氧糖的酶促水解中的非对映选择性和对映选择性高：牛油糖两种对映异构体的完全合成方法

  摘要：

  外消旋异丁基的微粒体环氧化物水解酶促进的水解3,4-脱水-2,6-二脱氧β-来苏-hexopyranoside，这是很容易从异丁基乙烯基醚制备和丁-3-烯-2-酮，具有非常发生高区域和对映体选择性，动力学拆分导致异丁基β-boivinoside的L和D形式，对映体过量均至少为96％。

  DOI：

  10.1039/c39860000007

文献信息

• A highly diastereoselective synthesis of dl-oleandrose
  作者：G. Berti、G. Catelani、F. Colonna、L. Monti

  DOI：10.1016/0040-4020(82)80194-4

  日期：1982.1

  between 4-methoxy-3-buten-2-one and isobutyl vinyl ether, which was converted into a mixture of the isobutyl β- and α-oleandrosides through hydroboration-oxidation. The latter reaction is highly diastereoselective since attack by borane takes place exclusively anti to the OMe group: none of the diasteroisomeric cymarosides are formed. The only side-products are small amounts of the isobutyl β- and α-amicetodies

  从4-甲氧基-3-丁烯-2-酮与异丁基乙烯基醚之间的狄尔斯-阿尔德加合物开始，得到外消旋的夹竹桃糖（2,6-二脱氧-3-O-甲基-阿拉伯-己酮）通过硼氢化反应氧化异丁基β-和α-油酸的混合物。后者的反应是高度非对映选择性的，因为硼烷的攻击仅对OMe基团发生：没有形成非对映异构环核苷。唯一的副产物是在硼氢化步骤中发生的脱甲氧基化作用形成的少量异丁基β-和α-酰胺基。
• High diastereo- and enantio-selectivity in the enzymatic hydrolysis of a racemic anhydrodeoxysugar: a totally synthetic approach to both enantiomers of boivinose
  作者：Pierluigi Barili、Giancarlo Berti、Giorgio Catelani、Fabrizia Colonna、Ettore Mastrorilli

  DOI：10.1039/c39860000007

  日期：——

  The microsomal epoxide hydrolase-promoted hydrolysis of racemic isobutyl 3,4-anhydro-2,6-dideoxy-β-lyxo-hexopyranoside, which is easily prepared from isobutyl vinyl ether and but-3-en-2-one, occurs with very high regio and enantio-selectivity, with kinetic resolution leading to the L-and D-forms of isobutyl β-boivinoside, both with an enantiomeric excess of at least 96%.

  外消旋异丁基的微粒体环氧化物水解酶促进的水解3,4-脱水-2,6-二脱氧β-来苏-hexopyranoside，这是很容易从异丁基乙烯基醚制备和丁-3-烯-2-酮，具有非常发生高区域和对映体选择性，动力学拆分导致异丁基β-boivinoside的L和D形式，对映体过量均至少为96％。
• Berti, Giancarlo; Catelani, Giorgio; Magi, Silvia, Gazzetta Chimica Italiana, 1980, vol. 110, # 2/3, p. 173 - 178
  作者：Berti, Giancarlo、Catelani, Giorgio、Magi, Silvia、Monti, Luigi

  DOI：——

  日期：——
• Berti, Giancarlo; Catelani, Giorgio; Colonna, Fabrizia, Gazzetta Chimica Italiana, <hi>1985</hi>, vol. 115, # 2, p. 85 - 90
  作者：Berti, Giancarlo、Catelani, Giorgio、Colonna, Fabrizia、Ferretti, Maria、Monti, Luigi

  DOI：——

  日期：——
• Synthesis of amicetose by three enantioselective methods
  作者：Lincoln A Noecker、Joseph A Martino、Paul J Foley、Diane M Rush、Robert M Giuliano、Frank J Villani

  DOI：10.1016/s0957-4166(97)00631-9

  日期：1998.1

  Three methods for the synthesis of the deoxy sugar amicetose (2,3,6-trideoxy-D-erythro-hexopyranoside) are described. All three utilize the known dihydropyran 2-isobutoxy-6-methyl-2,3-dihydro-4H-pyran as an intermediate. Asymmetric hydroboration of the dihydropyran with IpcBH(2) gave enantiomerically enriched isobutyl ex and beta-amicetosides. Hydroboration with borane-tetrahydrofuran followed by derivatization of the major product (beta-anomer) with R-(-)-1-(1-naphthyl)ethylisocyanate gave diastereomeric carbamates which were separated and converted to isobutyl beta-D and beta-L-amicetosides having high optical purity. Racemic isobutyl beta-amicetosides were also resolved by enzymatic transesterification using lipase and an acyl transfer reagent. Porcine pancreatic lipase and lipases from Candida rugosa and Pseudomonas sp. were evaluated in the presence of either vinyl acetate, vinyl butyrate, or trifluoroethyl butyrate as acylating agents. A GC-based method for determining enantiomeric purity of amicetose derivatives was developed. (C) 1998 Elsevier Science Ltd. All rights reserved.