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2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzoyl-3-O-(methoxycarbonyl)methyl-β-D-galactopyranoside | 178872-71-4

中文名称
——
中文别名
——
英文名称
2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzoyl-3-O-(methoxycarbonyl)methyl-β-D-galactopyranoside
英文别名
[(2R,3S,4S,5R,6R)-3,5-dibenzoyloxy-4-(2-methoxy-2-oxoethoxy)-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl benzoate
2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzoyl-3-O-(methoxycarbonyl)methyl-β-D-galactopyranoside化学式
CAS
178872-71-4
化学式
C35H40O11Si
mdl
——
分子量
664.781
InChiKey
ZRQNAHARGBUNEX-QNKNHBCRSA-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):
    4.93
  • 重原子数:
    47.0
  • 可旋转键数:
    14.0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.37
  • 拓扑面积:
    132.89
  • 氢给体数:
    0.0
  • 氢受体数:
    11.0

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:
    2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzoyl-3-O-(methoxycarbonyl)methyl-β-D-galactopyranoside三氟乙酸 作用下, 以 二氯甲烷 为溶剂, 反应 1.0h, 以95%的产率得到2,4,6-Tri-O-benzoyl-3-O-(methoxycarbonyl)methyl-D-galactopyranose
    参考文献:
    名称:
    Synthetic Studies on Sialoglycoconjugates 85: Synthesis of Sialyl Lewis X Ganglioside Analogs Containing a Variety of Anionic Substituents in Place of Sialic Acid
    摘要:
    Three sialyl-Le(X) ganglioside analogs containing carboxymethyl, sulfate, and phosphate groups in place of the sialic acid moiety, have been synthesized. Glycosylation of 2-(trimethylsilyl)ethyl O-(2,3,3-tri-O-benzyl-alpha-L-fucopyranosyl)-(1 --> 3) -O- (2-acetamido-6-O-benzyl-2-deoxy-beta-D-glucopyranosyl) - (1 --> 3) - 2,4,6-tri-O-benzyl-beta-D-galactopyranoside (10) with methyl 2,4,6-tri-O-benzoyl-3-O-(methoxycarbonyl)methyl-1-thio-beta-D-galactopyranoside (6) or methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-beta-D-galactopyranoside (9) using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, afforded the corresponding tetrasaccharide derivatives 11 and 19. Compounds 11 and 19 were converted into the alpha-trichloroacetimidates 14 and 23, via reductive removal of the benzyl and benzylidene groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (15) or 2-(tetradecyl)hexadecan-1-ol (24), gave the lipophilic derivatives 16 and 25. Compound 16 was transformed, via selective reduction of the azido group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title compound 18 in good yield. Compound 25 was treated with hydrazine acetate to give compound 26, which in turn was transformed, via sulfation or phosphorylation, and O-deacylation, into the target compounds 28 and 31.
    DOI:
    10.1080/07328309608005662
  • 作为产物:
    参考文献:
    名称:
    Synthetic Studies on Sialoglycoconjugates 85: Synthesis of Sialyl Lewis X Ganglioside Analogs Containing a Variety of Anionic Substituents in Place of Sialic Acid
    摘要:
    Three sialyl-Le(X) ganglioside analogs containing carboxymethyl, sulfate, and phosphate groups in place of the sialic acid moiety, have been synthesized. Glycosylation of 2-(trimethylsilyl)ethyl O-(2,3,3-tri-O-benzyl-alpha-L-fucopyranosyl)-(1 --> 3) -O- (2-acetamido-6-O-benzyl-2-deoxy-beta-D-glucopyranosyl) - (1 --> 3) - 2,4,6-tri-O-benzyl-beta-D-galactopyranoside (10) with methyl 2,4,6-tri-O-benzoyl-3-O-(methoxycarbonyl)methyl-1-thio-beta-D-galactopyranoside (6) or methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-beta-D-galactopyranoside (9) using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, afforded the corresponding tetrasaccharide derivatives 11 and 19. Compounds 11 and 19 were converted into the alpha-trichloroacetimidates 14 and 23, via reductive removal of the benzyl and benzylidene groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (15) or 2-(tetradecyl)hexadecan-1-ol (24), gave the lipophilic derivatives 16 and 25. Compound 16 was transformed, via selective reduction of the azido group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title compound 18 in good yield. Compound 25 was treated with hydrazine acetate to give compound 26, which in turn was transformed, via sulfation or phosphorylation, and O-deacylation, into the target compounds 28 and 31.
    DOI:
    10.1080/07328309608005662
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