phenyl 3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside | 179072-63-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside
• CAS: 179072-63-0
• 化学式: C₂₀H₂₄O₆S
• 分子量: 392.473
• InChiKey: GRZJDPNHABCZQR-RMMWZPCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.38
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-2-[(2R,4aR,6R,7R,8R,8aS)-6-(2-azido-ethoxy)-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Pentaerythritol as the Core of Multivalent Glycolipids:  Synthesis of a Glycolipid with Three SO₃Le^a Ligands

  摘要：

  [GRAPHICS]A glycolipid containing three SO(3)Le(a) ligands was synthesized with pentaerythritol as the core. The glycolipid was used to prepare glycoliposomes that showed stability similar to that of DSPC liposomes without glycolipid. The easily prepared derivatives of pentaerythritol proved to be useful scaffolds for multivalent displaying of carbohydrates in the form of glycolipids and clustered glycoliposomes.

  DOI：

  10.1021/ol0514202
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-1-硫代-β-D-苯基半乳糖苷 在 四丁基溴化铵 、 sodium methylate 作用下， 以 甲醇 、 氘代苯 为溶剂， 反应 0.5h， 生成 phenyl 3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Directing effect by remote electron-withdrawing protecting groups at O-3 or O-4 position of donors in glucosylations and galactosylations

  摘要：

  Glucosylations and galactosylations of various acceptors with donors possessing an electronwithdrawing benzylsulfonyl, benzoyl, or acetyl group at the O-3 or O-4 position were performed. A beta-directing effect by the benzylsulfonyl group at O-3 of the glucosyl donors and by the benzylsulfonyl and acyl groups at O-4 of the glucosyl donors was observed. In contrast, acyl groups at O-3 of the glucosyl donors and acyl groups at O-3 and O-4 of the galactosyl donors exhibited an alpha-directing effect. The alpha-directing effect is partly considered to remote participation of the acyl groups, whereas the beta-directing effect is somewhat attributed to the S(N)2-like reaction of the acceptor with the glycosyl triflate or the contact ion pair, which is stabilized by remote electron-withdrawing groups. Further evidence for the stability of the alpha-glycosyl triflates was determined by a low-temperature NMR study. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.014

文献信息

• Polymer-Supported Synthesis of a Branched Trisaccharide of the Type IA Group B Streptococcus Capsular Polysaccharide: 3-Iodo-4-methoxybenzyl as a New O-Protecting Group
  作者：Seema Mehta、Dennis M. Whitfield

  DOI：10.1016/s0040-4020(00)00612-8

  日期：2000.8

  independently synthesized and used to introduce this new protecting group. The levulinoyl and the IPMB protecting groups have been used in an orthogonal manner to create 3,4-branching on a galactopyranosyl residue. Due to the enhanced acid stability of the IPMB group over the PMB group, the former group was critical to the success of the synthesis. The final trisaccharide and its intermediates were cleaved

  描述了IA型B族链球菌荚膜多糖的关键分支三糖（1）的合成。使用了聚乙二醇（MeO–（CH 2 CH 2 O）n –H，MPEG）和二氧二甲苯[ p-（O）CH 2 –C 6 H 4 –CH 2（O）–，DOX]的单甲醚作为聚合物-载体/接头的组合。尝试在涉及N的糖基化条件下使用对甲氧基苄基（PMB）保护基-碘代琥珀酰亚胺/三氟甲磺酸银的促进作用导致碘化反应，形成了3-碘-4-甲氧基苄基（IPMB）衍生物。随后，独立地合成了IPMB氯化物，并用于引入该新的保护基。乙酰丙酰基和IPMB保护基已经以正交方式用于在半乳糖吡喃糖基残基上产生3，4-支链。由于IPMB组的酸稳定性高于PMB组，因此前一组对于合成成功至关重要。通过三氟甲磺酸scan（III）和乙酸酐从MPEG聚合物载体上裂解最终的三糖及其中间体。
• Orthogonal glycosylation strategy in synthesis of extended blood group B determinant
  作者：Osamu Kanie、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/0040-4039(96)00901-x

  日期：1996.6

  The orthogonal glycosylation strategy was applied for the synthesis of extended blood type B determinant (2) of a novel glycolipid 1. Key features in the synthesis are 1) four monosaccharide units were synthesized as either glycosyl fluoride or thioglycoside to be engaged to the orthogonal glycosylation strategy and 2) all necessary manipulations were completed at the monosaccharide level, therefore, manipulations during the elongation of sugar chain were minimized. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of the Sulfonate Analogue of Seminolipid via Horner−Wadsworth−Emmons Olefination
  作者：Laura Franchini、Federica Compostella、Diego Colombo、Luigi Panza、Fiamma Ronchetti

  DOI：10.1021/jo1008788

  日期：2010.8.6

  The first synthesis of the sulfonate analogue of seminolipid, the main sulfoglycolipid in mammalian sperm, is reported. Installation of the sulfonate unit was accomplished by a quite unexplored strategy based on Horner-Wadsworth-Emmons olefination on a 3'-keto-galactoside, followed by stereoselective double bond reduction.