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phenyl 2-O-methyl-1-thio-β-L-fucopyranoside | 261374-33-8

中文名称
——
中文别名
——
英文名称
phenyl 2-O-methyl-1-thio-β-L-fucopyranoside
英文别名
(2S,3S,4R,5S,6R)-5-methoxy-2-methyl-6-phenylsulfanyloxane-3,4-diol
phenyl 2-O-methyl-1-thio-β-L-fucopyranoside化学式
CAS
261374-33-8
化学式
C13H18O4S
mdl
——
分子量
270.35
InChiKey
QFXIBJJPFOYGJZ-ZYJFBCHUSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.3
  • 重原子数:
    18
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.54
  • 拓扑面积:
    84.2
  • 氢给体数:
    2
  • 氢受体数:
    5

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    phenyl 2-O-methyl-1-thio-β-L-fucopyranoside吡啶 、 10% Pd/C 、 zinc-copper couple 、 氢气sodium methylate溶剂黄146三氟甲烷磺酸甲酯 作用下, 以 四氢呋喃甲醇乙醚二氯甲烷 为溶剂, 20.0~70.0 ℃ 、400.01 kPa 条件下, 反应 37.5h, 生成 5-(methoxycarbonyl)pentyl 2-O-methyl-α-L-fucopyranosyl-(1→2)-4-O-methyl-β-D-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-α-D-galactopyranoside
    参考文献:
    名称:
    弓蛔虫幼虫及其类似物碳水化合物部分的合成、抗人血清抗原性和构效关系
    摘要:
    已经完成了生物素标记的寡糖部分的立体控制合成,该部分包含从寄生虫弓首蛔虫及其类似物的幼虫获得的 TES-糖蛋白抗原的 Galβ1-3GalNAc 核心。三糖 Fuc2Meα1-2Gal4Meβ1-3GalNAcα1-OR (A), Fucα1-2Gal4Meβ1-3GalNAcα1-OR (B), Fuc2Meα1-2Galβ1-3GalNAcα1-OR (C), Fucα1-2GalNAcα1-OR (C), Fucα1-2Galβ1-2Galβ1-2Galβ1-2Gal二糖 (A) -OR (E) (R = 生物素化探针) 使用 5-(甲氧基羰基) 戊基-2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基-(1→3)-通过嵌段合成合成2-azide-4-O-benzyl-2-deoxy-α-D-galactopyranoside 作为常见的糖基受体。我们通过酶联免疫吸附试验 (ELISA)
    DOI:
    10.3390/molecules17089023
  • 作为产物:
    描述:
    phenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-β-L-galactopyranoside 在 氢氧化钾磷酸 、 sodium hydride 、 zinc(II) chloride 作用下, 以 甲醇N,N-二甲基甲酰胺 为溶剂, 反应 18.5h, 生成 phenyl 2-O-methyl-1-thio-β-L-fucopyranoside
    参考文献:
    名称:
    Stereocontrolled Elaboration of Natural (−)-Polycavernoside A, a Powerfully Toxic Metabolite of the Red Alga Polycavernosa tsudai
    摘要:
    A stereoselective total synthesis of natural levorotatory polycavemoside A (1) has been achieved. initial investigations produced the properly activated disaccharide unit 18b via the conjoining of building blocks originating from L-fucose and D-xylose. This objective was followed by preparation of the phenylsulfonyl-substituted tetrahydropyran 23 and aldehyde 30. After proper linking of these key compounds, important information had to be garnered on the sequence of steps that would ultimately result in successful access to 1. Although oxidation to generate alpha-diketone 35 and unmasking of the C-13 hydroxyl did give rise efficiently to lactol 36, this functionality did not pave the way for ensuring macrolactonization. When this sequence of steps was reversed, it was indeed possible to arrive at the heavily functionalized precursor 43. However, numerous experiments failed to result in the requisite activation of C-16 for attachment of the trienyl side chain. However, if the E-vinyl iodide was elaborated in advance of alpha-diketone generation, glycosidation, and complete side chain construction, arrival at 1 proceeded without unsurmountable complications to furnish the targeted marine toxin.
    DOI:
    10.1021/ja993487o
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文献信息

  • Total Synthesis of the Triglycosyl Phenolic Glycolipid PGL-tb1 from<i>Mycobacterium tuberculosis</i>
    作者:Santiago Barroso、Riccardo Castelli、Marc P. Baggelaar、Danny Geerdink、Bjorn ter Horst、Eva Casas-Arce、Herman S. Overkleeft、Gijsbert A. van der Marel、Jeroen D. C. Codée、Adriaan J. Minnaard
    DOI:10.1002/anie.201206221
    日期:2012.11.19
    Complex: The synthesis of the glycolipid PGL‐tb1 present in the outer membrane of hypervirulent strains of Mycobacterium tuberculosis has been accomplished for the first time by using a highly convergent strategy featuring a Sonogashira coupling to unite a phenolic trisaccharide with the phthiocerol. Efficient asymmetric Cu‐catalyzed 1,4‐additions to unsaturated thioesters and cyclic enones have been
    复杂:结核分枝杆菌高毒力菌株外膜中糖脂PGL-tb1的合成首次通过高度融合的策略实现,该策略以Sonogashira偶联为特征,将酚三糖与苯硫酚结合在一起。高效的不对称铜催化不饱和硫酯和环状烯酮的1,4加成反应已用于引入甲基。
  • Stereocontrolled Elaboration of Natural (−)-Polycavernoside A, a Powerfully Toxic Metabolite of the Red Alga <i>Polycavernosa</i> <i>tsudai</i>
    作者:Leo A. Paquette、Louis Barriault、Dmitri Pissarnitski、Jeffrey N. Johnston
    DOI:10.1021/ja993487o
    日期:2000.2.1
    A stereoselective total synthesis of natural levorotatory polycavemoside A (1) has been achieved. initial investigations produced the properly activated disaccharide unit 18b via the conjoining of building blocks originating from L-fucose and D-xylose. This objective was followed by preparation of the phenylsulfonyl-substituted tetrahydropyran 23 and aldehyde 30. After proper linking of these key compounds, important information had to be garnered on the sequence of steps that would ultimately result in successful access to 1. Although oxidation to generate alpha-diketone 35 and unmasking of the C-13 hydroxyl did give rise efficiently to lactol 36, this functionality did not pave the way for ensuring macrolactonization. When this sequence of steps was reversed, it was indeed possible to arrive at the heavily functionalized precursor 43. However, numerous experiments failed to result in the requisite activation of C-16 for attachment of the trienyl side chain. However, if the E-vinyl iodide was elaborated in advance of alpha-diketone generation, glycosidation, and complete side chain construction, arrival at 1 proceeded without unsurmountable complications to furnish the targeted marine toxin.
  • Synthesis, Antigenicity Against Human Sera and Structure-Activity Relationships of Carbohydrate Moieties from Toxocara larvae and Their Analogues
    作者:Akihiko Koizumi、Kimiaki Yamano、Takashi Tsuchiya、Frank Schweizer、Fumiyuki Kiuchi、Noriyasu Hada
    DOI:10.3390/molecules17089023
    日期:——
    Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the Galβ1-3GalNAc core of the TES-glycoprotein antigen obtained from larvae of the parasite Toxocara and their analogues have been accomplished. Trisaccharides Fuc2Meα1-2Gal4Meβ1-3GalNAcα1-OR (A), Fucα1-2Gal4Meβ1-3GalNAcα1-OR (B), Fuc2Meα1-2Galβ1-3GalNAcα1-OR (C), Fucα1-2Galβ1-3GalNAcα1-OR (D) and a disaccharide Fuc2Meα1-2Gal4Meβ1-OR
    已经完成了生物素标记的寡糖部分的立体控制合成,该部分包含从寄生虫弓首蛔虫及其类似物的幼虫获得的 TES-糖蛋白抗原的 Galβ1-3GalNAc 核心。三糖 Fuc2Meα1-2Gal4Meβ1-3GalNAcα1-OR (A), Fucα1-2Gal4Meβ1-3GalNAcα1-OR (B), Fuc2Meα1-2Galβ1-3GalNAcα1-OR (C), Fucα1-2GalNAcα1-OR (C), Fucα1-2Galβ1-2Galβ1-2Galβ1-2Gal二糖 (A) -OR (E) (R = 生物素化探针) 使用 5-(甲氧基羰基) 戊基-2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基-(1→3)-通过嵌段合成合成2-azide-4-O-benzyl-2-deoxy-α-D-galactopyranoside 作为常见的糖基受体。我们通过酶联免疫吸附试验 (ELISA)
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