phenyl 2-O-allyl-1-thio-β-L-fucopyranoside | 1334671-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-allyl-1-thio-β-L-fucopyranoside
• 英文别名: (2S,3S,4R,5S,6R)-2-methyl-6-phenylsulfanyl-5-prop-2-enoxyoxane-3,4-diol
• CAS: 1334671-94-1
• 化学式: C₁₅H₂₀O₄S
• 分子量: 296.387
• InChiKey: KVRQUAHNVJGREK-INMIOYRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-allyl-1-thio-β-L-fucopyranoside 在 吡啶 、 二正丁基氧化锡 、 caesium carbonate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 47.0h， 生成 phenyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1→4)-2-O-allyl-3-O-benzyl-6-deoxy-1-thio-β-L-glucopyranoside
  参考文献：
  名称：

  使用 L-糖衍生的亲电子试剂通过异头 O-烷基化进行立体选择性 β-甘露糖基化

  摘要：

  实现了沙门氏菌血清群E1O-抗原的三糖重复单元的全合成。关键步骤涉及部分保护的 D-甘露糖与 L-岩藻糖衍生的 C4-三氟甲磺酸酯的 Cs 2 CO 3介导的异头O-烷基化，以 50% 的产率提供所需的 β-连接二糖。

  DOI：

  10.1002/ejoc.202100903
• 作为产物：
  描述：

  phenyl 3,4-O-isopropilidene-1-thio-β-L-fucopyranoside 在 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 phenyl 2-O-allyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of an O-sulfo LewisX analog as glycolipid antigen

  摘要：

  The title compound containing dihydroceramide as a ligand for CD1d was accomplished using the mannosyl, glucosaminyl, and fucosyl donors, and a sphinganine analogue, as suitable building blocks. The 2-O-unprotected mannosyl donor was coupled effectively with the sphinganine analog to afford the mannnosyl sphinganine derivative. The coupling of the glucosaminyl donor with the mannnosyl sphinganine acceptor required triflic acid as a promoter and the promoter change to silver triflate led to the undesired glycal production. The reduction of azide group using Zn powder was the key process, in which the amount of acetic acid was restricted to avoid the benzoyl migration and N-trichloroacetyl deprotection. The trisaccharide glycolipid was sulfonated at the 3-position of fucose moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.06.027

文献信息

• Synthesis of an O-sulfo LewisX analog as glycolipid antigen
  作者：Shuhei Ueno、Shigeomi Horito

  DOI：10.1016/j.carres.2011.06.027

  日期：2011.10

  The title compound containing dihydroceramide as a ligand for CD1d was accomplished using the mannosyl, glucosaminyl, and fucosyl donors, and a sphinganine analogue, as suitable building blocks. The 2-O-unprotected mannosyl donor was coupled effectively with the sphinganine analog to afford the mannnosyl sphinganine derivative. The coupling of the glucosaminyl donor with the mannnosyl sphinganine acceptor required triflic acid as a promoter and the promoter change to silver triflate led to the undesired glycal production. The reduction of azide group using Zn powder was the key process, in which the amount of acetic acid was restricted to avoid the benzoyl migration and N-trichloroacetyl deprotection. The trisaccharide glycolipid was sulfonated at the 3-position of fucose moiety. (C) 2011 Elsevier Ltd. All rights reserved.
• Stereoselective β‐Mannosylation via Anomeric <i>O</i> ‐Alkylation with L‐Sugar‐Derived Electrophiles
  作者：Ishani Lakshika Hettiarachchi、Shuai Meng、Mira Chahine、Xiaohua Li、Jianglong Zhu

  DOI：10.1002/ejoc.202100903

  日期：2021.12.28

  A total synthesis of the trisaccharide repeat unit of Salmonella serogroup E1 O-antigen is achieved. The key step involved the Cs2CO3-mediated anomeric O-alkylation of partially protected D-mannose with an L-fucose-derived C4-triflate to furnish desired β-linked disaccharide in 50 % yield.

  实现了沙门氏菌血清群E1O-抗原的三糖重复单元的全合成。关键步骤涉及部分保护的 D-甘露糖与 L-岩藻糖衍生的 C4-三氟甲磺酸酯的 Cs 2 CO 3介导的异头O-烷基化，以 50% 的产率提供所需的 β-连接二糖。