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(6S)-methyl 2,3,4-tri-O-benzyl<6-2H>-β-D-glucopyranoside | 118073-41-9

中文名称
——
中文别名
——
英文名称
(6S)-methyl 2,3,4-tri-O-benzyl<6-2H>-β-D-glucopyranoside
英文别名
(6S)-methyl 2,3,4-tri-O-benzyl<6-2H>-β-D-glucopyranoside;(6S)-<6-2H>Methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside;methyl 6-(S)-2,3,4-tri-O-benzyl-6-(2)H1-β-D-glucopyranoside;methyl 2,3,4-tri-O-benzyl-6(S)-β-D-(6-2H)glucopyranoside;(6S)-[6-2H]Methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside
(6S)-methyl 2,3,4-tri-O-benzyl<6-2H>-β-D-glucopyranoside化学式
CAS
118073-41-9
化学式
C28H32O6
mdl
——
分子量
465.551
InChiKey
MOKYEUQDXDKNDX-OSLUARELSA-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):
    4.11
  • 重原子数:
    34.0
  • 可旋转键数:
    11.0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.36
  • 拓扑面积:
    66.38
  • 氢给体数:
    1.0
  • 氢受体数:
    6.0

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

反应信息

  • 作为反应物:
    描述:
    (6S)-methyl 2,3,4-tri-O-benzyl<6-2H>-β-D-glucopyranoside 4 A molecular sieve 、 氢气氰化汞barium 、 mercury dibromide 作用下, 以 甲醇二氯甲烷溶剂黄146 为溶剂, 反应 30.5h, 生成 (6S)-<6-2H>Methyl -(2-6)-β-D-glucopyranoside
    参考文献:
    名称:
    Preferred conformation about the C5-C6 bond of N-acetylneuraminyl(2-6)-D-galacto- and -D-glucopyranosides in solution
    摘要:
    Diastereoselective deuteration and H-1 NMR spectroscopy were applied in a conformational study of the C5-C6 bond in four stereoisomeric methyl N-acetylneuraminyl(2-6)-beta-D-hexopyranosides [NeuNAc-alpha(2-6)Gal, NeuNAc-beta-(2-6)Gal, NeuNAc-alpha-(2-6)Glc, and NeuNAc-beta-(2-6)Glc]. In aqueous solution, NeuNAc-alpha-(2-6)Gal prefers a gt conformer (gg:gt:tg = ca. 20:60:20), NeuNAc(2-6)Glc isomers prefer a gg (gg:gt:tg = ca. 60:40:0), and NeuNAc-beta-(2-6)Gal exists equally in the three conformers.
    DOI:
    10.1021/jo00005a015
  • 作为产物:
    描述:
    6-(S)-6-(2)H1-1,6-anhydro-β-D-glucopyranose 以33%的产率得到(6S)-methyl 2,3,4-tri-O-benzyl<6-2H>-β-D-glucopyranoside
    参考文献:
    名称:
    Bock, Klaus; Pedersen, Henrik, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1988, vol. 42, # 3, p. 190 - 195
    摘要:
    DOI:
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文献信息

  • Stereoselective synthesis of chirally deuterated (S)-d-(6-2H1)glucose
    作者:Lin Xu、Neil P.J. Price
    DOI:10.1016/j.carres.2004.02.010
    日期:2004.4
    Chirally deuterated (S)-D-(6-(2)H(1))glucose has been prepared in good overall yield from d-(6,6'-(2)H(2))glucose by a short, five-step synthesis from D-(6,6-(2)H(2))glucose utilizing (R)-(+)-Alpine-Borane [(R)-9-[(6,6-dimethylbicyclo[3.1.1]hept-2-yl)methyl]-9-borabicyclo[3.3.1]nonane]. Suitably protected methyl 2,3,4-tri-O-benzyl-D-(6,6-(2)H(2))glucopyranoside was prepared and the deuterated O-6 primary
    从d-(6,6'-(2)H(2))葡萄糖中短短五次制备手性代(S)-D-(6-(2)H(1))葡萄糖即可获得良好的总收率D((6,6-(2)H(2))葡萄糖利用(R)-(+)-高山-硼烷[(R)-9-[(6,6-二甲基双环[3.1.1] [庚-2-基)甲基] -9-环[3.3.1]壬烷]。制备适当保护的甲基2,3,4-三-O-苄基-D-(6,6-(2)H(2))葡萄糖苷,并通过Swern氧化将代的O-6伯醇氧化为醛。用非代(R)-(+)-Alpine-Borane进行立体选择性还原得到甲基2,3,4-tri-O-苄基-(6S)-D-(6-(2)H(1))葡萄糖苷在标准条件下脱保护,得到标题化合物。关键的立体选择性还原步骤以90%的收率实现。准备使用经济,
  • The Function of the 5-Hydroxymethyl Group of Lactose in Enzymatic Hydrolysis with beta-Galactosidase from E. coli.
    作者:Kim Adelhorst、Klaus Bock、S. T. Thiilborg、H. M. Nielsen、Fatima M. Piedade、M. M. Kady、S. Brøgger Christensen
    DOI:10.3891/acta.chem.scand.46-1114
    日期:——
    A series of 6-substituted methyl lactoside derivatives together with methyl allolactoside and (6S)-methyl [6-H-2]lactoside have been synthesized and characterized by NMR spectroscopy. All compounds were tested as substrates for the enzyme beta-galactosidase from E. coli using progress curve kinetic methology both in single-substrate and competition experiments. The results show that the hydrolysis of methyl lactoside to a large extent takes place through an intramolecular trans-glycosidation reaction via allolactoside. Furthermore, methyl 6-amino-6-deoxy-D-glucopyranoside proved to be an inhibitor for the enzymatic hydrolysis.
  • OHRUI, HIROSHI;NISHIDA, YOSHIHIRO;ITOH, HISASHI;MEGURO, HIROSHI, J. ORG. CHEM., 56,(1991) N, C. 1726-1731
    作者:OHRUI, HIROSHI、NISHIDA, YOSHIHIRO、ITOH, HISASHI、MEGURO, HIROSHI
    DOI:——
    日期:——
  • BOCK, KLAUS;PEDERSEN, HENRIK, ACTA CHEM. SCAND., 42,(1988) N 3, 190-195
    作者:BOCK, KLAUS、PEDERSEN, HENRIK
    DOI:——
    日期:——
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