1,2-Di-O-acetyl-3,5,6-tri-O-benzyl-α,β-D-glucofuranose | 51515-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-Di-O-acetyl-3,5,6-tri-O-benzyl-α,β-D-glucofuranose
• 英文别名: 1,2-Di-O-acetyl-3,5,6-tri-O-benzyl-D-glucofuranose；[(3R,4S,5R)-2-acetyloxy-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-4-phenylmethoxyoxolan-3-yl] acetate
• CAS: 51515-91-4
• 化学式: C₃₁H₃₄O₈
• 分子量: 534.606
• InChiKey: MDBYGPQILSBDGC-JCLUOYIWSA-N

物化性质

• 沸点：
  628.1±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-Di-O-acetyl-3,5,6-tri-O-benzyl-α,β-D-glucofuranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 24.0h， 生成 benzyl 3,5,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-β-D-glucofuranoside
  参考文献：
  名称：

  The synthesis and characterisation of 2-O-(6-O-l-glycero-α,β-d-manno-heptopyranosyl-α-d-glycopyranosyl)- α,β-d-glucopyranose

  摘要：

  The title compounds were synthesised, and appropriate derivatives were characterised by GLC, GLC-MS, and NMR spectroscopy. The GLC and GLC-MS data proved 2-O-(6-O-L-glycero-alpha-D-manno-heptopyranosyl-alpha-D-glucopyranosyl)-D-glucopyranose to be a constituent of the outer-core region of the lipopolysaccharide from Escherichia coli K-12, indicating the heptosyl residue to be linked to the terminal glucopyranose residue.

  DOI：

  10.1016/s0008-6215(00)90992-3
• 作为产物：
  描述：

  溴甲苯 在 sodium hydride 、 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 40.0h， 生成 1,2-Di-O-acetyl-3,5,6-tri-O-benzyl-α,β-D-glucofuranose
  参考文献：
  名称：

  Koell, Peter; John, Hans-Georg; Schulz, Juergen, Liebigs Annalen der Chemie, 1982, # 4, p. 613 - 625

  摘要：

  DOI：

文献信息

• Synthesis of <i>C</i>-Glycosyl Lactones and Protected <i>C</i>-Glycosyl Amino Acids:  Use of Radical Cyclization
  作者：Junhu Zhang、Derrick L. J. Clive

  DOI：10.1021/jo981435w

  日期：1999.2.1

  halogen on the adjacent carbon, were condensed with (2,2-diphenylhydrazono)acetic acid (2); the resulting esters undergo radical cyclization to afford carbohydrates fused to a 2,2-diphenylhydrazino lactone unit (6c,d-13c,d). In suitable cases (9c,d) such carbohydrate lactones can be elaborated into C-glycosyl amino acids.

  将保护的碳水化合物6a-13a与（2,2-二苯基肼基）乙酸（2）缩合，所述保护的碳水化合物6a-13a在相邻的碳上具有一个游离羟基和苯基硒烯基或卤素。所得酯进行自由基环化，得到与2，2-二苯基肼基内酯单元（6c，d-13c，d）融合的碳水化合物。在合适的情况下（9c，d），这种碳水化合物内酯可以被精加工成C-糖基氨基酸。
• Allyl protecting group mediated intramolecular aglycon delivery (IAD): synthesis of α-glucofuranosides and β-rhamnopyranosides
  作者：Ian Cumpstey、Antony J. Fairbanks、Alison J. Redgrave

  DOI：10.1016/j.tet.2004.07.083

  日期：2004.10

  The use of allyl protecting group mediated intramolecular aglycon delivery (IAD) as a strategy for intramolecular glycosylation has been extended to allow the stereoselective synthesis of α-glucofuranosides and β-rhamnopyranosides, in a totally stereoselective fashion. The efficiency of intramolecular glycosylation is dependent on the protecting group pattern of the glycosyl donor, and on the steric

  使用烯丙基保护基介导的分子内糖苷配基（IAD）作为分子内糖基化的策略已得到扩展，以完全立体选择性的方式允许α-葡糖呋喃糖苷和β-鼠李糖吡喃糖苷的立体选择性合成。分子内糖基化的效率取决于糖基供体的保护基团模式以及糖基受体的空间体积。
• Synthesis and Glycosidic Reaction of 1,2-Anhydromanno-, Lyxo-, Gluco-, and Xylofuranose Perbenzyl Ethers
  作者：Yuguo Du、Fanzuo Kong

  DOI：10.1080/07328309608005693

  日期：1996.9

  Stereospecific synthesis of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers was successfully achieved via intramolecular S(N)2 reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonates, were prepared from the corresponding 1,2-diols and tosyl chloride under phase transfer conditions in good yields. Condensation of the anhydro sugars with 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose or N-benzyloxycarbonyl L-serine methyl ester in the absence of catalyst gave 1,2-trans-linked glycofuranosides in high yield.