(2S,3S)-1-O-benzyl-1,2,3-butanetriol | 93367-12-5

• 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,3S)-1-O-benzyl-1,2,3-butanetriol
• 英文别名: (2S,3S)-1-phenylmethoxybutane-2,3-diol
• CAS: 93367-12-5
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: ANKPCTWGDMEUSH-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二对甲苯磺酸戊乙二醇 、 (2S,3S)-1-O-benzyl-1,2,3-butanetriol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以6.67 g的产率得到(2S,3S)-2-Benzyloxymethyl-3-methyl-1,4,7,10,13,16-hexaoxa-cyclooctadecane
  参考文献：
  名称：

  Sasaki, Shigeki; Kawasaki, Motoji; Koga, Kenji, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 10, p. 4247 - 4266

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,3R)-1-(benzyloxy)-4-(tert-butylthio)-2,3-butanediol 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 trimethoxonium tetrafluoroborate 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 (2S,3S)-1-O-benzyl-1,2,3-butanetriol
  参考文献：
  名称：

  Selective transformation of 2,3-epoxy alcohols and related derivatives. Strategies for nucleophilic attack at carbon-1

  摘要：

  DOI：

  10.1021/jo00350a050

文献信息

• A One‐Pot Two‐Step Enzymatic Pathway for the Synthesis of Enantiomerically Enriched Vicinal Diols
  作者：Pier Paolo Giovannini、Michel Müller、Francesco Presini、Serena Baraldi、Daniele Ragno、Graziano Di Carmine、Christian Jacoby、Giovanni Bernacchia、Olga Bortolini

  DOI：10.1002/ejoc.202001542

  日期：2021.2.12

  this report a ThDP‐dependent lyase (Ao : DCPIP OR) and a NADH‐dependent reductase (AAR) have been consecutively employed in two steps without intermediate work‐up and purification, affording enantiomerically enriched 1,2‐diols in good yield (up to 78 %). The reductase cloning and overexpression is herein reported for the first time.

  的多样化文库顺-1,2-二醇具有由unprecedent单釜两步协议被成功制备。在本报告中，ThDP依赖的裂解酶（Ao：DCPIP OR）和NADH依赖的还原酶（AAR）已连续两个步骤使用，而无需进行中间处理和纯化，从而以良好的收率提供了对映体富集的1,2-二醇（高达78％）。本文首次报道了还原酶的克隆和过表达。
• 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。
• 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.
• BEHRENS, C. H.;KO, S. Y.;SHARPLESS, K. B.;WALKER, F. J., J. ORG. CHEM., 1985, 50, N 26, 5687-5696
  作者：BEHRENS, C. H.、KO, S. Y.、SHARPLESS, K. B.、WALKER, F. J.

  DOI：——

  日期：——