ethyl 4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside | 160243-08-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside
• CAS: 160243-08-3
• 化学式: C₂₂H₂₆O₅S
• 分子量: 402.511
• InChiKey: GEJKHUZPROPERW-RMJIQZSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-(trimethylsilyl)ethyl 2-O-benzyl-α-L-fucopyranolyl-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Tetrasaccharide Repeating Unit of the O‐Antigen from Enterohemorrhagic Escherichia coli O157 in the form of its 2‐(trimethylsilyl)ethyl Glycoside

  摘要：

  Two alpha-linked disaccharide derivatives, ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl-(1 -> 2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-alpha-D-mannopyranoside (10) and 2-(trimethylsilyl)ethyl 3-O-acetyl-4-O-benzoyl-2-O-benzyl-alpha-L-fucopyranosyl-(1 -> 4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-beta-D-glucopyranoside (16), were prepared from appropriate monosaccharide synthons. The disaccharide 16 was deacetylated and debenzoylated to afford the acceptor 17, which was allowed to react with the donor 10 to afford a tetrasaccharide derivative 18. This tetrasaccharide was transformed in three steps into 21, the desired repeating unit of the antigen from enterohemorrhagic E. coli type O157.

  DOI：

  10.1080/07328300500495878
• 作为产物：
  描述：

  (2R,3S,4R,5S,6S)-3-Benzyloxy-5-(dimethoxy-phenyl-methoxy)-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-ol 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.5h， 以2.48 g的产率得到ethyl 4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of Tetrasaccharide Repeating Unit of the O‐Antigen from Enterohemorrhagic Escherichia coli O157 in the form of its 2‐(trimethylsilyl)ethyl Glycoside

  摘要：

  Two alpha-linked disaccharide derivatives, ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl-(1 -> 2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-alpha-D-mannopyranoside (10) and 2-(trimethylsilyl)ethyl 3-O-acetyl-4-O-benzoyl-2-O-benzyl-alpha-L-fucopyranosyl-(1 -> 4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-beta-D-glucopyranoside (16), were prepared from appropriate monosaccharide synthons. The disaccharide 16 was deacetylated and debenzoylated to afford the acceptor 17, which was allowed to react with the donor 10 to afford a tetrasaccharide derivative 18. This tetrasaccharide was transformed in three steps into 21, the desired repeating unit of the antigen from enterohemorrhagic E. coli type O157.

  DOI：

  10.1080/07328300500495878

文献信息

• Synthesis of the 5-aminopentyl glycoside of β-d-Galp-(1 → 4)-β-d-GlcpNAc-(1 → 3)-l-Fucp and fragments thereof related to glycopeptides of human Christmas factor and the marine sponge Microciona prolifera
  作者：Thomas Ziegler

  DOI：10.1016/0008-6215(94)84179-9

  日期：1994.9

  The marine sponge Microciona prolifera and human coagulation factor IX (Christmas factor)-related mono- to tri-saccharide 5-aminopentyl glycosides beta-D-Gal p-R (5), beta-D-Glc pNAc-R (16), beta-D-Gal p-(1-->4)-beta-D-Glc p NAc-R (26), beta-D-Glc p NAc-(1-->3)-beta-L-Fuc p-R (39), beta-D-Glc pNAc-(1-->3)-alpha-L-Fuc p-R (43), beta-D-Gal p-(1-->4)-beta-D- Glc pNAc-(1-->3)-beta-L-Fuc p-R (45), and beta-D-Gal

  海洋海绵Microciona增殖和人类凝血因子IX（圣诞节因子）相关的单糖至三糖5-氨基戊基糖苷β-D-GalpR（5），β-D-GlcpNAc-R（16），β- D-Gal p-（1-> 4）-beta-D-Glc p NAc-R（26），beta-D-Glc p NAc-（1-> 3）-beta-L-Fuc pR（39 ），β-​​D-GlcpNAc-（1-> 3）-α-L-FucpR（43），β-D-Galp-（1-> 4）-β-D-GlcpNAc-（ 1-> 3）-beta-L-Fuc pR（45）和beta-D-Gal p-（1-> 4）-beta-D-Glc p NAc-（1-> 3）-alpha制备了-L-Fuc pR（47），其中R是5-氨基戊氧基间隔基，其允许糖缀合物的构建。因此，3,4,6-三-O-乙酰基-2-脱氧-2-（2,2,2-三氯乙氧基羰基-氨基）-α-D-吡喃葡萄糖基三氯乙酰亚氨酸盐（10）和1
• Chemical Synthesis of the Nonreducing Hexasaccharide Fragment of Axinelloside A Based on a Stepwise Glycosylation Approach
  作者：Su-Jia Li、Qing Fang、Ying-Wen Huang、Yi-Yang Luo、Xiao-Dong Mu、Ling Li、Xiao-Chen Yin、Jin-Song Yang

  DOI：10.1021/acs.orglett.2c02618

  日期：2022.10.7

  An expedient synthesis of the nonreducing hexasaccharide fragment of axinelloside A has been completed via a linear stepwise glycosylation approach. Challenges involved in the synthesis include the highly stereoselective construction of five consecutive 1,2-cis-glycosidic linkages and the formation of a sterically crowded 2,3-disubstituted l-fucoside subunit. Protecting group-directing glycosylation

  axinelloside A 的非还原性六糖片段的权宜合成已通过线性逐步糖基化方法完成。合成中涉及的挑战包括五个连续的 1,2-顺式糖苷键的高度立体选择性构建和空间拥挤的 2,3-二取代的l-岩藻糖苷亚基的形成。保护基团导向糖基化策略，例如苯甲酰基取代基的远程参与效应和 4,6- O-亚苄基的立体控制效应，用于合成所需的 1,2-顺式糖苷键。此外，2,3-支链l-岩藻糖苷框架是通过 3- O建立的然后是 2 - O糖基化序列，其中核心l-岩藻糖单元的 3-羟基首先被糖基化，然后是 2-羟基。合成六糖得到适当保护，因此可以用作合成其天然形式的前体。
• Acid-promoted synthesis of per-O-sulfated fucooligosaccharides related to fucoidan fragments
  作者：Vadim B. Krylov、Zinaida M. Kaskova、Dmitry Z. Vinnitskiy、Nadezhda E. Ustyuzhanina、Alexey A. Grachev、Alexander O. Chizhov、Nikolay E. Nifantiev

  DOI：10.1016/j.carres.2011.01.005

  日期：2011.4

  has been performed with the use of previously reported acid-promoted protocol for per-O-sulfation of polyols by SO(3) complexes. During the treatment of (1-->3)-linked oligofucosides under these conditions with the promotion by TfOH, the unusual rearrangement of the reducing pyranose residue into furanose one was observed. To avoid the formation of rearrangement by-products, the use of a series of strong

  与不同类型的天然岩藻依聚糖相关的二，四，六，八，十二和十六烷全过氧硫酸化衍生物的合成已使用先前报道的酸促进方案进行了合成。通过SO（3）配合物对多元醇进行O-硫酸化。在这些条件下，在TfOH的促进下处理（1-> 3）连接的寡糖苷，观察到还原的吡喃糖残基异常重排为呋喃糖。为避免形成重排副产物，研究了使用一系列强酸作为大寡糖苷的硫酸化促进剂，并基于使用TFA代替TfOH制定了改进的方案。通过十二烷基和十六烷基葡糖苷的全-O-硫酸化衍生物的合成证明了该新方法的效率。
• Convenient synthesis of sulfated oligofucosides
  作者：Chengli Zong、Zhongzhen Li、Tiantian Sun、Peng Wang、Ning Ding、Yingxia Li

  DOI：10.1016/j.carres.2010.04.006

  日期：2010.7

  Two types of sulfated octyl tetra- to octaoligofucosides with different sulfation patterns were synthesized employing a combination of stepwise elongation and convergent strategies in which trichloroacetimidates and thioglycosides were selected as the glycosyl donors. (C) 2010 Elsevier Ltd. All rights reserved.