phenyl 3-O-benzyl-1-thio-β-D-glucopyranoside | 189144-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: Phenyl 3-O-benzyl-b-D-thioglucopyranoside；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-4-phenylmethoxy-6-phenylsulfanyloxane-3,5-diol
• CAS: 189144-54-5
• 化学式: C₁₉H₂₂O₅S
• 分子量: 362.447
• InChiKey: LPMBAPQCLQUXNK-QQXKLLMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-benzyl-1-thio-β-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 tetrafluoroboric acid 、 2,6-二叔丁基-4-甲基吡啶 、 zinc chloride diethyl ether 、 1,1-二氯甲醚 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 氢气 、 sodium methylate 、 sodium acetate 、 silver trifluoromethanesulfonate 、 sodium hydride 、 一水合肼 、 溶剂黄146 、 palladium dichloride 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 23.0 ℃ 、1.38 MPa 条件下， 反应 127.83h， 生成 6-[(2S,3R,4S,5S,6R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanehydrazide
  参考文献：
  名称：

  Synthesis of Kojidextrins and Their Protein Conjugates. Incidence of Steric Mismatch in Oligosaccharide Synthesis

  摘要：

  Kojidextrins are biologically important oligosaccharides that are involved in many physiological processes including protein glycosylation and bacterial growth. As part of our project to explore the role kojidextrins may play in bacterial pathogenesis, here we report Synthetic routes to kojibiose (54), -triose (58), -tetraose (64), and -pentaose (69) equipped with alpha-linked (hydrazinocarbonyl)-pentyl aglycon, using linear and convergent strategies. In the search for a rapid convergent strategy for the construction of extended kojidextrins, four kojibiose donors (1-4) were synthesized that contain acyl- and ether-type protecting groups in various ratios. These were tested to probe the influence of diverse protecting group assemblies on their glycosyl donor ability. Attempted condensation of these donors with kojitriose and -tetraose accepters failed to give the desired products apparently because of steric mismatch between the donor and the acceptor moieties. A one-pot procedure was developed for the covalent attachment of the synthetic saccharides through their hydrazido group to human serum albumin (HSA) using Tietze's squarate method to give neoglycoproteins containing up to 28 saccharide units per HSA.

  DOI：

  10.1021/jo962300y
• 作为产物：
  描述：

  3-O-苄基-1,2:5,6-O-双异丙叉-α-D-呋喃葡萄糖 在 三氟化硼乙醚 、 sodium ethanolate 、 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 phenyl 3-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  First Synthesis of a Trisaccharide of Glycosylkaemferide: A Resistance Factor in Carnations

  摘要：

  A trisaccharide, phenyl beta-D-glucopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 6)]-1-thio-beta-D-glucopyranoside, of glycosylkaemferide, a resistance factor in carnations, was synthesized in a practical way.

  DOI：

  10.1081/scc-120027259

文献信息

• A Modular Strategy Toward the Synthesis of Heparin-like Oligosaccharides Using Monomeric Building Blocks in a Sequential Glycosylation Strategy
  作者：Jeroen D. C. Codée、Bas Stubba、Marialuisa Schiattarella、Herman S. Overkleeft、Constant A. A. van Boeckel、Jacques H. van Boom、Gijsbert A. van der Marel

  DOI：10.1021/ja045613g

  日期：2005.3.1

  A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building blocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems

  描述了一种新的灵活组装策略，用于肝素和硫酸乙酰肝素的模块化合成。报道的策略使用单体构建块来构建寡糖链以获得最大程度的灵活性。在组装中，使用三氟甲磺酸锍激活剂系统将 1-羟基葡糖叠氮基和 1-硫代糖醛酸供体结合在连续糖基化方案中。关键的 1-硫代糖醛酸是以有效的方式从双丙酮葡萄糖中获得的，采用部分保护的葡萄糖和艾糖硫糖苷的化学和区域选择性氧化。
• Strict Stereocontrol by 2,4-<i>O</i>-Di-<i>tert</i>-butylsilylene Group on β-Glucuronylations
  作者：Takayuki Furukawa、Hiroshi Hinou、Shin-Ichiro Nishimura

  DOI：10.1021/ol300634x

  日期：2012.4.20

  Strict beta-controlled glucuronylations without classical neighboring-group participation were achieved by the assistance of a 2,4-O-di-tert-butylsilylene group. Comparison of activation conditions and conformational analysis indicated that the strict beta-selectivity was achieved by steric hindrance of the 2,4-O-di-tert-butylsilylene group and not by complex glycosyl intermediates.
• Synthesis of benzyl protected β-d-GlcA-(1→2)-α-d-Man thioglycoside building blocks for construction of Cryptococcus neoformans capsular polysaccharide structures
  作者：Lorenzo Guazzelli、Rebecca Ulc、Stefan Oscarson

  DOI：10.1016/j.carres.2014.01.022

  日期：2014.5

  In a project targeting the synthesis of large oligosaccharide structures corresponding to the Cryptococcus neoformans GXM capsular polysaccharide, an easy access to thiodisaccharide building blocks comprising a beta-linked glucuronic acid moiety and a 6-O-acetyl group was required. Several pathways to such building blocks have been investigated, addressing the problem of constructing a beta-linked glucuronic acid residue protected with groups that are orthogonal to a primary acetyl group. Two efficient routes have been developed, one using benzoylated glucosyl donors to form the beta-linkage followed by a change of protecting groups to benzyls and subsequent introduction of the carboxyl function and the acetyl group. The second route explored the possibility to achieve beta-selectivity using glucuronyl donors without acyl protecting groups. BF3- etherate promoted glycosylations with benzyl (2,3,4-tri-O-benzyl-alpha-D-glucupyranosyl)uronate trichloroacetimidate in the presence of nitrile solvents and at low temperatures reproducibly gave good yields of disaccharides with high beta-selectivity. Furthermore, the use of recently reported glucuronyl thioglycoside donors protected with a cyclic 2,4-silylene acetal was found to represent another efficient and completely beta-selective way to desired disaccharide building blocks. (C) 2014 Elsevier Ltd. All rights reserved.
• First Synthesis of a Trisaccharide of Glycosylkaemferide: A Resistance Factor in Carnations
  作者：Mamoru Koketsu、Motoaki Kuwahara、Hisako Sakurai、Hideharu Ishihara

  DOI：10.1081/scc-120027259

  日期：2004.1

  A trisaccharide, phenyl beta-D-glucopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 6)]-1-thio-beta-D-glucopyranoside, of glycosylkaemferide, a resistance factor in carnations, was synthesized in a practical way.
• Synthesis of Kojidextrins and Their Protein Conjugates. Incidence of Steric Mismatch in Oligosaccharide Synthesis
  作者：Vince Pozsgay、Eric P. Dubois、Lewis Pannell

  DOI：10.1021/jo962300y

  日期：1997.5.1

  Kojidextrins are biologically important oligosaccharides that are involved in many physiological processes including protein glycosylation and bacterial growth. As part of our project to explore the role kojidextrins may play in bacterial pathogenesis, here we report Synthetic routes to kojibiose (54), -triose (58), -tetraose (64), and -pentaose (69) equipped with alpha-linked (hydrazinocarbonyl)-pentyl aglycon, using linear and convergent strategies. In the search for a rapid convergent strategy for the construction of extended kojidextrins, four kojibiose donors (1-4) were synthesized that contain acyl- and ether-type protecting groups in various ratios. These were tested to probe the influence of diverse protecting group assemblies on their glycosyl donor ability. Attempted condensation of these donors with kojitriose and -tetraose accepters failed to give the desired products apparently because of steric mismatch between the donor and the acceptor moieties. A one-pot procedure was developed for the covalent attachment of the synthetic saccharides through their hydrazido group to human serum albumin (HSA) using Tietze's squarate method to give neoglycoproteins containing up to 28 saccharide units per HSA.