(2S,3R)-1-(benzyloxy)-2,3-butanediol | 99666-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-1-(benzyloxy)-2,3-butanediol
• 英文别名: 1-O-benzyl-2S,3R-butane-2,3-diol；(2S,3R)-1-phenylmethoxybutane-2,3-diol
• CAS: 99666-01-0
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: ANKPCTWGDMEUSH-KOLCDFICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1-(benzyloxy)-2,3-butanediol 生成 (2S,3R)-1-(benzyloxy)-2,3-butanediol diacetate
  参考文献：
  名称：

  BEHRENS, C. H.;KO, S. Y.;SHARPLESS, K. B.;WALKER, F. J., J. ORG. CHEM., 1985, 50, N 26, 5687-5696

  摘要：

  DOI：
• 作为产物：
  描述：

  顺式-1,2-二羟甲基乙烯 生成 (2S,3R)-1-(benzyloxy)-2,3-butanediol
  参考文献：
  名称：

  实用的对映体特异性合成（+）erythro-9-（2s-hydroxy-3r-nonyl）腺嘌呤。

  摘要：

  报道了从L-抗坏血酸，L（+）酒石酸和Z-丁烯1,4-二醇合成1S（2S-苄氧基乙基）环氧乙烷（9）的三种对映体特异性化合物。还描述了从9到2S-羟基-3R-壬胺的转化（19）。

  DOI：

  10.1016/s0040-4039(01)91182-7

文献信息

• A new unusual C-1 substitution of 2,3 epoxy alcohols with LiI: regio and stereoselective obtaining of 1-iodo 2,3 diols and 2,3-diols
  作者：Carlo Bonini、Claudio Giuliano、Giuliana Righi、Leucio Rossi

  DOI：10.1016/s0040-4039(00)60207-1

  日期：1992.11

  2,3 epoxy alcohols ( and ) underwent an unusual substitution at C-1, with the use of excess LiI at 70°, affording the corresponding 1-iodo-2,3 diols. Starting with (E) 2,3 epoxy alcohols the stereochemistry of the final diols was demonstrated to be ; a possible mechanism, based on some experimental data, is also showed.

  2,3环氧醇（和）在C-1处进行了不寻常的取代，在70°下使用了过量的LiI，得到了相应的1-io-2,3二醇。从（E）2,3环氧醇开始，最终二醇的立体化学被证明是：根据一些实验数据，还显示了一种可能的机制。
• Selective transformation of 2,3-epoxy alcohols and related derivatives. Strategies for nucleophilic attack at carbon-1
  作者：Carl H. Behrens、Soo Y. Ko、K. Barry Sharpless、Frederick J. Walker

  DOI：10.1021/jo00350a050

  日期：1985.12
• C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Applications and Synthesis of Naturally Occurring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide
  作者：Carlo Bonini、Chiara Federici、Leucio Rossi、Giuliana Righi

  DOI：10.1021/jo00120a025

  日期：1995.7

  The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly. In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or three stereochemistry starting from trans or cis epoxy alcohols. Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occurring (S,S)-2,3-octanediol and (R,R)-muricatacin. The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides. The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols. This methodology has been applied to the asymmetric synthesis of naturally occurring pheromones like 3(R)-octanol and 4(R)-dodecanolide.