2,3-di-O-acetyl-1,6-anhydro-β-D-glucose | 22331-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 2,3-di-O-acetyl-1,6-anhydro-β-D-glucose
• 英文别名: [(1R,2R,3S,4R,5R)-4-acetyloxy-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-3-yl] acetate
• CAS: 22331-11-9
• 化学式: C₁₀H₁₄O₇
• 分子量: 246.217
• InChiKey: DNDHCEAGSOQRRM-HOTMZDKISA-N

物化性质

• 沸点：
  355.0±42.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-di-O-acetyl-1,6-anhydro-β-D-glucose 在 palladium on activated charcoal 吡啶 、 silver trifluoromethanesulfonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 2,3-di-O-acetyl-1,6-anhydro-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)-β-D-glucopyranose
  参考文献：
  名称：

  Design and Synthesis of 2‘-Deoxy-2‘-Fluorodisaccharides as Mechanism-Based Glycosidase Inhibitors That Exploit Aglycon Specificity

  摘要：

  Stable, aglycon-specific inactivators of glycosidases have considerable potential as fools in the study of mechanisms of oligosaccharide processing, and possibly as avenues toward new therapeutics. Glycosidases for which the rate-determining step with the natural substrate is the hydrolysis of the glycosyl-enzyme intermediate are shown to be inactivated by the 2'-deoxy-2'-fluoro derivative of this substrate. Thus Agrobacterium faecalis beta-glucosidase is inactivated by 2'-deoxy-2'-fluorocellobiose according to inactivation parameters of k(i) = 0.018 min(-1) and K-i = 20 mM. Inactivation is shown to occur via the accumulation of the same 2-deoxy-2-fluoroglycosyl-enzyme intermediate as that formed using activated 2-deoxy-2-fluoroglycosides by identification of the labeled peptide in proteolytic digests. Thus, interactions between the enzyme and the sugar aglycon provide sufficient transition state stabilization to allow formation and trapping of the glycosyl-enzyme. beta-Glucocerebrosidase, a beta-glucosidase specific for hydrolysis of glucocerebrosides, is not inactivated by 2'-deoxy-2'-fluorocellobiose, thereby demonstrating the aglycon specificity of this class of inactivator.

  DOI：

  10.1021/ja9627454
• 作为产物：
  描述：

  1,6-脱水-β-D-葡萄糖-2,3,4-三邻醋酸 生成 2,3-di-O-acetyl-1,6-anhydro-β-D-glucose
  参考文献：
  名称：

  ZEMEK, JIRI;KUCAR, STEFAN;ZAMOCKY, JURAJ

  摘要：

  DOI：

文献信息

• Synthesis of the Repeating Unit of the Capsular Polysaccharide of Streptococcus Pneumoniae Type 3 as a Building Block Suitable for Formation of Oligomers
  作者：Per. Garegg、Stefan Oscarson、Ulf Tedebark

  DOI：10.1080/07328309808002339

  日期：1998.5.1

  The synthesis of a cellobiouronic thioglycoside donor 12, protected with a selectively removable 3′-O-benzyl group is described. The donor 12 is suitable as a monomer building block in the construction of oligomer structures corresponding to the capsular polysaccharide of Streptococcus pneumoniae type 3. The carboxyl function was introduced through regioselective TEMPO-oxidation of a 4′,6′-diol cellobiose

  描述了由可选择性去除的3'- O-苄基保护的纤维二糖硫糖苷供体12的合成。供体12适合作为构建对应于3型肺炎链球菌荚膜多糖的低聚物结构中的单体结构单元。通过对4'，6'-二醇纤维二糖衍生物的区域选择性TEMPO-氧化来引入羧基官能团。如果在2,3,2'，3'，4'，6'-己醇衍生物上进行氧化，则还观察到仲2-羟基和3-羟基的氧化，得到三羧基衍生物作为主要化合物之一产品。硫代糖苷是通过1，6-脱水桥的酸性巯基分解形成的。捐助者12 通过与间隔醇进行糖基化和随后的脱苄基反应，将其转化为合适的起始单体受体。
• 2′-fluoromaltose: Synthesis and properties of 4-O-(2-deoxy-2-fluoro-α-d-glucopyranosyl)-d-glucopyranose, and the crystal structure of 2,3-di-O-acetyl-1,6-anhydro-4-O-(3,4-tri-O-acetyl-2-deoxy-2-fluoro-α-d-glucopyranosyl)-β-d- glucopyranose
  作者：Judith G. Shelling、David Dolphin、Peter Wirz、Roger E. Cobbledick、Frederick W.B. Einstein

  DOI：10.1016/0008-6215(84)85222-2

  日期：1984.9

  d -glucopyranosyl)-β- d -glucopyranose. Deprotection of this disaccharide gave 2′-deoxy-2′-fluoromaltose. Maltose and its fluorinated analogue displayed similar 1 H- and 13 C-n.m.r. spectra and optical rotations, indicating that these two sugars are isomorphous in solution and suggesting that 2′-deoxy-2′-fluoromaltose might be a suitable substrate for studies of α-glycosidases.

  3,4,6-三-O-乙酰-2-脱氧-2-氟-α-d-吡喃葡萄糖基溴化物与3,4,6-三-O-乙酰-2-脱氧-2-氟-溴的偶联在两种情况下，在Koenigs-Knorr反应条件下，α-d-吡喃半乳糖基溴化物与2,3-二-O-乙酰基-1,6-脱水-β-d-葡萄糖一起生成仅相应的α-（1→4 ）-连接的二糖。在第一种情况下，通过1 H-和19 Fn.mr以及X-射线晶体学分析2,3-二-O-乙酰基-1,6-脱水4-O-（3， 4,6-三-O-乙酰基-2-脱氧-2-氟-α-d-吡喃葡萄糖基）-β-d-吡喃葡萄糖。该二糖的脱保护得到2'-脱氧-2'-氟麦芽糖。麦芽糖及其氟化类似物显示出相似的1 H和13 Cn.mr光谱和旋光度，
• Synthetic Studies on Oligosaccharide of a Glycolipid from the Spermatozoa of Bivalves. VII. The Synthesis of Di-, Tri-, Tetrasaccharides Related to Glycosphinogolipid.
  作者：Tadahiro TAKEDA、Noriyasu HADA、Yukio OGIHARA

  DOI：10.1248/cpb.40.1930

  日期：——

  The three kinds of oligosaccharides that constitute the partial structure of lipid IV (1) were synthesized as follows. The disaccharide O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (13), the trisaccharide O-α-D-mannopyranosyl-(1→3)-O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (21), and the tetrasaccharide O-α-D-mannopyranosyl-(1→3)-O-[β-D-xylopyranosyl-(1→2)]-O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (25) were each synthesized by stepwise condensation of suitably protected monosaccharide units. A 1, 6-anhydro-D-glucopyranose derivative was used as the glycosyl acceptor, and bromide derivatives of D-mannose and D-xylose as donors.

  构成脂质 IV 部分结构（1）的三种寡糖合成如下。二糖 O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (13)，三糖 O-α-D-mannopyranosyl-(1→3)-O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (21)、和四糖 O-α-D-吡喃甘露糖基-(1→3)-O-[β-D-吡喃木糖基-(1→2)]-O-β-D-吡喃甘露糖基-(1→4)-D-吡喃葡萄糖（25）都是通过逐步缩合适当保护的单糖单元合成的。1，6-脱水-D-吡喃葡萄糖衍生物用作糖基受体，D-甘露糖和 D-木糖的溴化物衍生物用作供体。
• Zemek, Jiri; Kucar, Stefan; Anderle, Dusan, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 9, p. 2347 - 2352
  作者：Zemek, Jiri、Kucar, Stefan、Anderle, Dusan

  DOI：——

  日期：——
• Kucar, Stefan; Zamocky, Juraj; Zemek, Juraj, Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 8, p. 1780 - 1787
  作者：Kucar, Stefan、Zamocky, Juraj、Zemek, Juraj、Anderle, Dusan、Matulova, Maria

  DOI：——

  日期：——