phenyl 2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside | 503065-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside
• CAS: 503065-76-7
• 化学式: C₁₅H₂₀O₄S
• 分子量: 296.387
• InChiKey: YOEZBAWYJHTIPW-DDNMXHNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside 在 sodium hydride 、 二正丁基氧化锡 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 65.0h， 生成 phenyl 3,4-di-O-benzyl-2-O-(4-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside
  参考文献：
  名称：

  Direct Synthesis of the β-l-Rhamnopyranosides

  摘要：

  [GRAPHICS]The direct formation Of beta-L-rhamnopyranosides by means of thioglycoside donors protected with a 2-O-sulfonate ester and, ideally, a 4-O-benzoyl ester, is reported. Activation is achieved with the combination of 1-benzenesulfinyl piperidine and triflic anhydride in the presence of 2,4,6-tri-tert-butylpyrimidine. Selectivities vary from moderate to good, and the sulfonyl group is easily removed post-glycosylation with sodium amalgam in 2-propanol.

  DOI：

  10.1021/ol0340890
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 在 对甲苯磺酸 氢氧化钾 、 氢溴酸 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙酸酐 、 丙酮 、 乙腈 为溶剂， 反应 16.0h， 生成 phenyl 2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively

  摘要：

  Two analogues of the Le(x) trisaccharide, alpha-L-Fucp -(1 --> 3)-[beta-D-Galp -(1 --> 4)]-D-Glcp were synthesized as allyl glycosides. In these derivatives either only the N-acetylglucosamine is replaced by glucose or both the N-acetylglucosamine and the facosyl residue are replaced by glucose and rhamnose, respectively. Our synthetic scheme used armed beta-thiophenyl fuco- and rhamnoside glycosyl donors that were prepared anomerically pure from the corresponding alpha-glycosyl bromides. The protecting groups were chosen to allow access to the fully deprotected trisaccharides without reduction of the allyl glycosidic group. These analogues will be used as soluble antigens in binding experiments with anti-Le(x) antibodies and can also be conjugated to a carrier protein and used as immunogens. In the course of this synthetic work, we also describe the use of reversed-phase HPLC to purify key protected trisaccharide intermediates prior to their deprotection. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00053-3

文献信息

• From <scp>l</scp>-Rhamnose to Rare 6-Deoxy-<scp>l</scp>-Hexoses
  作者：Someswara Rao Sanapala、Suvarn S. Kulkarni

  DOI：10.1021/acs.orglett.6b01796

  日期：2016.8.5

  Efficient and rapid transformation of cheaply available l-rhamnose into all the isomeric 6-deoxy-l-hexoses via regio- and stereoselective nucleophilic displacements of triflates is reported. The synthesis entails regioselective protections, one-pot double displacements of triflates, and cascade inversions. The methodology allows facile access to all the rare 6-deoxy-l-hexoses as stable thioglycoside

  据报道，通过三氟甲烷磺酸的区域和立体选择性亲核置换，可以将廉价的1-鼠李糖高效快速地转化为所有异构的6-脱氧-1-己糖。合成需要区域选择性保护，三平面的一锅双位移和级联反演。该方法允许容易地获得所有罕见的6-脱氧-1-己糖作为稳定的硫代糖苷结构单元。
• Total Synthesis of the Repeating Units of <i>Proteus penneri</i> 26 and <i>Proteus vulgaris</i> TG155 via a Common Disaccharide
  作者：Ankita Paul、Suvarn S. Kulkarni

  DOI：10.1021/acs.orglett.3c01618

  日期：2023.6.16

  Herein, we report the first total synthesis of the trisaccharide and tetrasaccharide repeating units of P. penneri 26 and P. vulgaris TG155, respectively, having a common disaccharide unit, 3-α-l-QuipNAc-(1 → 3)-α-d-GlcpNAc-(1 →. Striking features of the targets are the presence of rare sugar units, l-quinovosamine and l-rhamnosamine, all joined through α-glycosidic linkages. Major challenges in the

  在此，我们报道了P. penneri 26 和P. vulgaris TG155 的三糖和四糖重复单元的首次全合成，分别具有共同的二糖单元 3-α- l -Qui p NAc-(1 → 3)- α- d -Glc p NAc-(1 →。目标的显着特征是稀有糖单元、 L-奎诺糖胺和L-鼠李糖胺的存在，它们均通过 α-糖苷键连接。形成 1,2 的主要挑战- d-葡萄糖胺、 L-奎诺糖胺和d-半乳糖胺中的顺式糖苷键已得到解决。
• [EN] A METHOD FOR SYNTHESIS OF 6-DEOXY-L-HEXOSES FROM L-RHAMNOSE<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE 6-DÉSOXY-L-HEXOSES À PARTIR DE L-RHAMNOSE
  申请人：INDIAN INST TECHNOLOGY BOMBAY

  公开号：WO2018002957A8

  公开（公告）日：2018-07-19