(R)-2-hydroxy-3-((4-methoxybenzyl)oxy)propyl 4-methylbenzenesulfonate | 1122091-19-3

• 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: (R)-2-hydroxy-3-((4-methoxybenzyl)oxy)propyl 4-methylbenzenesulfonate
• CAS: 1122091-19-3
• 化学式: C₁₈H₂₂O₆S
• 分子量: 366.435
• InChiKey: BCRJZNWOFRIPOH-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-2-hydroxy-3-((4-methoxybenzyl)oxy)propyl 4-methylbenzenesulfonate 在 咪唑 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (S)-tert-butyl((1-((4-methoxybenzyl)oxy)but-3-en-2-yl)oxy)dimethylsilane
  参考文献：
  名称：

  A flexible organocatalytic enantioselective synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its congeners

  摘要：

  A unified enantioselective route is developed for the synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its synthetic congeners. A proline-catalyzed aminoxylation, cross-metathesis, Wittig reaction, and catalytic dihydroxylation are key steps of this synthesis. This new approach is envisioned to facilitate the synthesis of every representative member of the family with skeletal and stereochemical variation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.058
• 作为产物：
  描述：

  3-[(4-甲氧基苯基)甲氧基]丙醛 在 吡啶 、 sodium tetrahydroborate 、 copper(ll) sulfate pentahydrate 、 L-脯氨酸 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 (R)-2-hydroxy-3-((4-methoxybenzyl)oxy)propyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  A flexible organocatalytic enantioselective synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its congeners

  摘要：

  A unified enantioselective route is developed for the synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its synthetic congeners. A proline-catalyzed aminoxylation, cross-metathesis, Wittig reaction, and catalytic dihydroxylation are key steps of this synthesis. This new approach is envisioned to facilitate the synthesis of every representative member of the family with skeletal and stereochemical variation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.058

文献信息

• Preparation of Optically Active 1-<i>O</i>-Alkyl-3-<i>O</i>-arylsulfonyl-<i>sn</i>-glycerol Derivatives: Substrate Engineering in Enzyme-Mediated Enantioselective Hydrolysis
  作者：Kazutsugu Matsumoto、Yasutaka Shimada、Hiroshi Sato、Sachiyo Mochizuki

  DOI：10.1055/s-0028-1083632

  日期：2008.12

  Lipase PS catalyzes the enantioselective hydrolysis of various2-acetyl compounds of the 1- O-alkyl-3- O-arylsulfonyl- SN-glycerolderivatives to afford the corresponding optically active compounds.Changing the structure of the 1- O-alkyland 3- O-arylsulfonyl groups affects boththe reactivity and enantioselectivity. Finally, the E value of the reaction for 2-acetyl-3- O-3,5-dimethylbenzenesulfonyl-1-

  脂肪酶 PS 催化 1-O-烷基-3-O-芳基磺酰基-SN-甘油衍生物的各种 2-乙酰基化合物的对映选择性水解，得到相应的旋光化合物。 改变 1-O-烷基和 3-O- 的结构芳基磺酰基影响反应性和对映选择性。最后，2-乙酰基-3-O-3,5-二甲基苯磺酰基-1-O-4-甲氧基苄基-SN-甘油反应的E值大于200。
• The impact of lysyl-phosphatidylglycerol on the interaction of daptomycin with model membranes
  作者：Ryan Moreira、Scott D. Taylor

  DOI：10.1039/d2ob01384c

  日期：——

  l))] (lysyl-PG) and mutations to the proteins directly involved in the synthesis and translocation of lysyl-PG are implicated in resistance mechanisms. To study the interaction of daptomycin with lysyl-DMPG-containing model membranes a new stereospecific and regioselective synthesis of lysyl-DMPG was developed. Studies on model membranes containing lysyl-DMPG demonstrate that: (1) daptomycin is not

  达托霉素是一种重要的临床抗生素，其耐药性正在上升。金黄色葡萄球菌的达托霉素耐药菌株通常具有增加的 1,2-二酰基-sn-甘油-3-[phospho-1-(3-lysyl(1-glycerol))] (lysyl-PG) 和直接参与赖氨酰-PG 合成和易位的蛋白质突变与耐药机制有关。为了研究达托霉素与含有赖氨酰-DMPG 的模型膜的相互作用，开发了一种新的赖氨酰-DMPG 立体特异性和区域选择性合成。对含有赖氨酰-DMPG 的模型膜的研究表明：(1) 达托霉素不会被赖氨酰-DMPG 的阳离子电荷显着排斥；(2) 与 DMPG 相比，达托霉素与赖氨酰-DMPG 的结合强度较低；(3) 赖氨酰-DMPG 的存在不会显着影响达托霉素的膜结合主链构象；(4) lysyl-DMPG 增加寡聚体形成；(5) 赖氨酰-DMPG 不影响赖氨酰-PG 的模型膜流动性：与达托霉素抗性相关的 PG 比率。
• Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine
  作者：Yasutaka Shimada、Kazumasa Usuda、Hirokazu Okabe、Tsuguru Suzuki、Kazutsugu Matsumoto

  DOI：10.1016/j.tetasy.2009.11.005

  日期：2009.12

  The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates. (C) 2009 Elsevier Ltd. All rights reserved.