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

• 分子结构分类: 有机化合物 - 有机氧化合物
• 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
• CAS: 118073-41-9
• 化学式: C₂₈H₃₂O₆
• 分子量: 465.551
• InChiKey: MOKYEUQDXDKNDX-OSLUARELSA-N

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

反应信息

• 作为反应物：
  描述：

  (6S)-methyl 2,3,4-tri-O-benzyl<6-2H>-β-D-glucopyranoside 在 钯 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：

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氘代（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-硼环[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））吡喃葡萄糖苷，并通过Swern氧化将氘代的O-6伯醇氧化为醛。用非氘代（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））吡喃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：——