o-methoxycarbonylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside | 1101186-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: o-methoxycarbonylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: methyl 2-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]sulfanylbenzoate
• CAS: 1101186-14-4
• 化学式: C₄₂H₄₂O₇S
• 分子量: 690.857
• InChiKey: ZITDLDHIXXPJIW-SRDZHKAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  97.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  o-methoxycarbonylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 、 3-O-(2',3',4'-tri-O-benzyl-β-D-galactopyranosyl)-1,2-di-O-(4-methoxybenzyl)-sn-glycerol 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.25h， 以69%的产率得到3-O-[(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-(2',3',4'-tri-O-benzyl-β-D-galactopyranosyl)]-1,2-di-O-(4-methoxybenzyl)-sn-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
• 作为产物：
  描述：

  硫代水杨酸甲酯 在 sodium methylate 、 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 o-methoxycarbonylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside
  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

• Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis
  作者：Hirofumi Dohi、Risa Sakurai、Manami Tamura、Ryota Komai、Yoshihiro Nishida

  DOI：10.1080/07328303.2021.1921787

  日期：2021.3.31
• 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.