(2S)-2,3-di-p-methoxybenzyl glycerol | 190779-65-8

• 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)-2,3-di-p-methoxybenzyl glycerol
• 英文别名: 2,3-di-O-(4-methoxybenzyl)-sn-glycerol；(2S)-2,3-bis[(4-methoxyphenyl)methoxy]propan-1-ol
• CAS: 190779-65-8
• 化学式: C₁₉H₂₄O₅
• 分子量: 332.397
• InChiKey: GGYBAISFYJUZIK-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2,3-di-p-methoxybenzyl glycerol 在 2,6-二甲基吡啶 、 正丁基锂 、 4 A molecular sieve 、 三氟化硼乙醚 、 四丁基硫酸氢铵 、 臭氧 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 26.08h， 生成 1-dethia-3-(p-methoxybenzyloxy)-1-oxacepham
  参考文献：
  名称：

  Strategies for the Formation of 1-Dethia-1-oxa-cephams

  摘要：

  The paper describes three possible routes for the formation of 1-dethia-1-oxa-cephams. The first two routes: (a) [2+2]cycloaddition to chiral vinyl ethers and (b) condensation of 4-acetoxyazetidin-2-one to chiral alcohols, are followed by the ring closure step involving N-alkylation. The third route (c) consists of N-alkylation prior to the cyclization step. In order to compare routes (a), (b) and (c), diastereomeric 1-dethia-3-(4-methoxybenzyloxy)-1-oxacephams were synthesized using three possible strategies. While the comparison of stereoselectivities of the [2+2]cycloaddition method (a) and the condensation (b) shows unequivocally the advantage of the former, the route (c) leads to the reverse direction of asymmetric induction relative to the first two steps and offers the highest asymmetric induction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00405-1
• 作为产物：
  描述：

  1,2-di-O-(4-methoxybenzyl)-3-O-trityl-sn-glycerol 在 Amberlyst 15E ion-exchange resin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以80%的产率得到(2S)-2,3-di-p-methoxybenzyl glycerol
  参考文献：
  名称：

  Synthesis and absolute structures of Mycoplasma pneumoniae β-glyceroglycolipid antigens

  摘要：

  just recently, a pair of beta-glycolipids was isolated from the cell membrane of Mycoplasma pneumoniae as a mixture of the two compounds. They are the major immunodeterminants of this pathogenic Mycoplasma and indicate high medicinal potential. They have a beta-(1 -> 6)-linked disaccharide structure close to each other: one has beta-D-galactopyranoside (beta-Gal-type 1) at the non-reducing terminal, and another has beta-D-glucopyranoside (beta-Glc-type 2). In the present Study, the first stereoselective synthesis was conducted for each of the two beta-glycolipids 1 and 2. H-1 NMR and TLC-immunostaining studies of the synthetic compounds enable LIS to establish the absolute structures having the beta-(1 -> 6)-linked disaccharides at the glycerol sn-3 position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.028

文献信息

• Synthesis of 3″,4″-bisphosphate-containing analogs of adenophostin A
  作者：Nicole C.R. van Straten、Nicole M.A.J. Kriek、Zsolt A.C. Cziria、Gijsbert A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4020(97)00309-8

  日期：1997.5

  Glycosylation of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-alpha/beta-D-glucopyranoside (6) with tert-butyldiphenylsilylglycol (7) or 1,2-di-O-p-methoxybenzyl-sn-glycerol (16) under the agency of N-iodosuccinimide/triflic acid afforded alpha-glucosides 8 and 17, respectively. Protective group manipulations (8 --> 10 and 17 --> 20) and acetolysis of the methylthiomethyl functions yielded 2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-1-O-acetoxymethylglycol (11) and 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-2-O-acetoxymethyl-1-O-tert-butyldiphenylsilyl-sn-glycerol (21). Vorbruggen condensation with silylated 6-N-benzoyladenine (22), subsequent protective group manipulations on 23 and 29 followed by phosphorylation furnished, after purification, homogeneous glycol-based adenophostin A analog 4 and glycerol-based analog 5. (C) 1997 Elsevier Science Ltd.
• Synthesis and absolute structures of Mycoplasma pneumoniae β-glyceroglycolipid antigens
  作者：Akira Miyachi、Atsushi Miyazaki、Yuko Shingu、Kazuhiro Matsuda、Hirofumi Dohi、Yoshihiro Nishida

  DOI：10.1016/j.carres.2008.09.028

  日期：2009.1

  just recently, a pair of beta-glycolipids was isolated from the cell membrane of Mycoplasma pneumoniae as a mixture of the two compounds. They are the major immunodeterminants of this pathogenic Mycoplasma and indicate high medicinal potential. They have a beta-(1 -> 6)-linked disaccharide structure close to each other: one has beta-D-galactopyranoside (beta-Gal-type 1) at the non-reducing terminal, and another has beta-D-glucopyranoside (beta-Glc-type 2). In the present Study, the first stereoselective synthesis was conducted for each of the two beta-glycolipids 1 and 2. H-1 NMR and TLC-immunostaining studies of the synthetic compounds enable LIS to establish the absolute structures having the beta-(1 -> 6)-linked disaccharides at the glycerol sn-3 position. (C) 2008 Elsevier Ltd. All rights reserved.
• Strategies for the Formation of 1-Dethia-1-oxa-cephams
  作者：Z Kałuża、B Furman、P Krajewski、M Chmielewski

  DOI：10.1016/s0040-4020(00)00405-1

  日期：2000.7

  The paper describes three possible routes for the formation of 1-dethia-1-oxa-cephams. The first two routes: (a) [2+2]cycloaddition to chiral vinyl ethers and (b) condensation of 4-acetoxyazetidin-2-one to chiral alcohols, are followed by the ring closure step involving N-alkylation. The third route (c) consists of N-alkylation prior to the cyclization step. In order to compare routes (a), (b) and (c), diastereomeric 1-dethia-3-(4-methoxybenzyloxy)-1-oxacephams were synthesized using three possible strategies. While the comparison of stereoselectivities of the [2+2]cycloaddition method (a) and the condensation (b) shows unequivocally the advantage of the former, the route (c) leads to the reverse direction of asymmetric induction relative to the first two steps and offers the highest asymmetric induction. (C) 2000 Elsevier Science Ltd. All rights reserved.