6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl chloride | 120444-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl chloride
• 英文别名: [(2R,3R,4S,5R,6S)-6-chloro-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 120444-53-3
• 化学式: C₂₉H₃₁ClO₆
• 分子量: 511.015
• InChiKey: WOLMTVURXQGEOM-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl chloride 在 2,4,6-三甲基吡啶 、 silver perchlorate 、 氯 作用下， 以 乙醚 、 氘代氯仿 为溶剂， 反应 0.75h， 生成 O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranosyl chloride
  参考文献：
  名称：

  异麦芽寡糖和相关化合物的甲基α-糖苷的系统化学合成和nmr光谱。

  摘要：

  1,6-脱水-2,3,4-三-O-苄基-β-D-吡喃葡萄糖的酸催化硫酚氧化反应和所得苯基2,3,4-三-O-苄基-1-硫代-苯甲酸乙酰化α-D-吡喃葡萄糖苷（4）得到苯基6-O-乙酰基-2,3,4-三-O-苄基-1-硫代-α-D-吡喃葡萄糖苷（5）。5与氯的反应立体定向产生相应的β-糖基氯，将其在高氯酸银和2,4,6-三甲基吡啶的存在下用4处理，得到苯基O-（6-O-乙酰基-2,3 ，4-三-O-苄基-α-D-吡喃葡萄糖基）-（1-6）-2,3,4-三-O-苄基-1-硫代-α-D-吡喃葡萄糖苷（17）。结晶O-（6-O-乙酰基-2,3,4-三-O-苄基-α-D-吡喃葡萄糖基）-（1 ---- 6）-2,3,4-三-O-苄基- β-D-吡喃葡萄糖基氯，可以通过用氯处理以立体特异性的方式容易地从17中获得，在异麦芽寡糖，直至并包括八糖的甲基糖苷的嵌段合成中，“苯丙氨酸”用作关键糖基（异麦芽糖基）供体。通过使用SnCl2活化的2

  DOI：

  10.1016/0008-6215(88)80008-9
• 作为产物：
  描述：

  1,6-酸酐-2,3,4-三-O-苄基-β-D-吡喃葡萄糖 在 吡啶 、 氯 、 对甲苯磺酸 作用下， 以 氘代氯仿 为溶剂， 反应 2.25h， 生成 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl chloride
  参考文献：
  名称：

  异麦芽寡糖和相关化合物的甲基α-糖苷的系统化学合成和nmr光谱。

  摘要：

  1,6-脱水-2,3,4-三-O-苄基-β-D-吡喃葡萄糖的酸催化硫酚氧化反应和所得苯基2,3,4-三-O-苄基-1-硫代-苯甲酸乙酰化α-D-吡喃葡萄糖苷（4）得到苯基6-O-乙酰基-2,3,4-三-O-苄基-1-硫代-α-D-吡喃葡萄糖苷（5）。5与氯的反应立体定向产生相应的β-糖基氯，将其在高氯酸银和2,4,6-三甲基吡啶的存在下用4处理，得到苯基O-（6-O-乙酰基-2,3 ，4-三-O-苄基-α-D-吡喃葡萄糖基）-（1-6）-2,3,4-三-O-苄基-1-硫代-α-D-吡喃葡萄糖苷（17）。结晶O-（6-O-乙酰基-2,3,4-三-O-苄基-α-D-吡喃葡萄糖基）-（1 ---- 6）-2,3,4-三-O-苄基- β-D-吡喃葡萄糖基氯，可以通过用氯处理以立体特异性的方式容易地从17中获得，在异麦芽寡糖，直至并包括八糖的甲基糖苷的嵌段合成中，“苯丙氨酸”用作关键糖基（异麦芽糖基）供体。通过使用SnCl2活化的2

  DOI：

  10.1016/0008-6215(88)80008-9

文献信息

• Inhibitors of <i>endo</i>-α-mannosidase. Part III. Congeners of 1-deoxy-3-<i>O</i>-(α-<scp>D</scp>-glucopyranosyl)-mannojirimycin modified in the glucose unit
  作者：Ulrike Spohr、Mimi Bach

  DOI：10.1139/v93-241

  日期：1993.11.1

  The syntheses of congeners of 1-deoxy-3-O-(α-D-glucopyranosyl)-mannojirimycin (1), a strong inhibitor of the glycoprotein-processing endo-mannosidase, are described. The chemical modifications of 1 involved all monodeoxy-genations and mono-O-methylations of the glucose unit and the replacement of this unit by D-galactose, D-xylose, and 2-chloro-2-deoxy-D-glucose. As reported previously, none of the modifications of 1, including deoxygenations and O- and N-methylations of the deoxymannojirimycin unit, improved the inhibitory properties, but demonstrated the high specificity in the recognition of 1 by the enzyme and allowed the assignment of intermolecular hydrogen bonds of the inhibitor • enzyme complex. Essential for complex formation were found NH-5, OH-2, OH-4, and OH-6 of the DMJ unit, as well as OH-3′, OH-4′, and CH₂-6′ of the glucose unit. The residual activities on deoxygenating the OH-2′ and OH-6′ groups of 1 suggest their involvement at the periphery of the binding site.

  描述了一种强烈抑制糖蛋白处理内切脱甲基酶的1-去氧-3-O-(α-D-葡萄糖吡喃基)-曼诺基霉素（1）同系物的合成。1的化学改性包括所有单去氧基化和单-O-甲基化葡萄糖单元以及将该单元替换为D-半乳糖、D-木糖和2-氯-2-脱氧-D-葡萄糖。正如先前报道的那样，1的所有改性，包括去氧化和去氧曼诺基霉素单元的O-和N-甲基化，都没有改善抑制性能，但表明了对酶识别1的高特异性，并允许分配抑制剂•酶复合物的分子间氢键。复合物形成所需的关键部位包括DMJ单元的NH-5、OH-2、OH-4和OH-6，以及葡萄糖单元的OH-3′、OH-4′和CH2-6′。对于1的OH-2′和OH-6′基团的去氧化残余活性表明它们参与了结合位点的外围。
• One-pot α-glycosylation pathway via the generation in situ of α-glycopyranosyl imidates in N,N-dimethylformamide
  作者：Yuko Shingu、Akira Miyachi、Yoshiko Miura、Kazukiyo Kobayashi、Yoshihiro Nishida

  DOI：10.1016/j.carres.2005.07.020

  日期：2005.10

  Divergent pathways are disclosed in the activation or 2-O-benzyl-1-hydroxy sugars by a reagent combination of CBr4 and Ph3P, all of which afford one-pot alpha-glycosylation methods. When this reagent is used in CH2Cl2, the 1-hydroxy sugar is converted to the alpha-glycosyl bromide in a conventional way and leads to the one-pot a-glycosylation method based on a halide ion-catalytic mechanism. In either DMF or a mixture of DNIF and CHCl3, however, alternative a-glycosyl species are generated. Front the H-1 and C-13 NMR study of the products, as well as the reactions using Vilsmeier reagents [(CH3)(2)N'=CHX]X (X Br and Cl). these were identified as cationic alpha-glycopyranosyl imidates having either Br or Cl counter ion, The cationic alpha-glycosyl imidate (Br), derived specifically in the presence of DMF, is more reactive than the alpha-glycosyl bromide and thus is responsible for the accelerated one-pot alpha-glycosylation. The one-pot alpha-glycosylation methodology performed in DMF was assessed also with different types of acceptor substrates including tertiary alcohols and an anomeric mixture of 1-OH sugars, (C) 2005 Elsevier Ltd. All rights reserved.
• KOVAC, PAVOL;LERNER, LAURA, CARBOHYDR. RES., 184,(1988) C. 87-112
  作者：KOVAC, PAVOL、LERNER, LAURA

  DOI：——

  日期：——