1,6-脱水-2,4-O-苯基-Β-D-吡喃葡萄糖 | 33208-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,6-脱水-2,4-O-苯基-Β-D-吡喃葡萄糖
• 英文名称: 1,6-anhydro-2,4-di-O-benzyl-β-D-glucopyranose
• 英文别名: 1,6-anhydro-2,4-di-O-benzyl-beta-D-glucopyranose；(1R,2S,3S,4R,5R)-2,4-bis(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octan-3-ol
• CAS: 33208-48-9
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: MXNWLHBKIGOLJO-USYVTKNRSA-N

物化性质

• 熔点：
  103 °C
• 沸点：
  509.8±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6-脱水-2,4-O-苯基-Β-D-吡喃葡萄糖 在 双(三甲基硫化硅) 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2,4-di-O-benzyl-1-thio-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis of α-Glycosyl Thiols by Stereospecific Ring-Opening of 1,6-Anhydrosugars

  摘要：

  Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of a-glycosyl thiols. All the reactions were highly stereoselective and afforded the a-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding a-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to a-glycosyl thiols of great value was established.

  DOI：

  10.1021/jo202069y
• 作为产物：
  描述：

  1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α- and β-D-glucopyranose 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 3.5h， 生成 1,6-脱水-2,4-O-苯基-Β-D-吡喃葡萄糖
  参考文献：
  名称：

  Schmidt, Richard R.; Michel, Josef; Ruecker, Ernst, Liebigs Annalen der Chemie, 1989, p. 423 - 428

  摘要：

  DOI：

文献信息

• Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects
  作者：Jacob St‐Gelais、Émilie Côté、Danny Lainé、Paul A. Johnson、Denis Giguère

  DOI：10.1002/chem.202002825

  日期：2020.10.21

  glucopyranose analogues at positions C‐2, C‐3, C‐4, and C‐6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C‐6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies

  在这项工作中，我们在位置C-2，C-3，C-4和C-6上合成了所有的单氟，双氟和三氟吡喃葡萄糖类似物。这项系统的研究使我们能够对氟化葡萄糖类似物的19 F共振进行直接比较，并确定它们的亲脂性。在C-6处带有氟原子的化合物通常是最亲水的，而具有邻位多氟基序的化合物则是最亲脂的。最后，使用密度泛函理论首次评估了氟化葡萄糖类似物的溶剂化能。此方法允许的日志 P氟葡萄糖类似物的预测，这是可比较的C日志 P从各种基于网络的方案获得的值。
• Ring-opening polymerization of new 3-O-branched 1, 6-anhydro glucopyranose di- and trisaccharide monomers
  作者：Chaolumen Bai、Davaanyam Budragchaa、Takashi Yoshida

  DOI：10.1016/j.carres.2017.04.017

  日期：2017.6

  6-anhydro disaccharide monomers were polymerized. However, the polymerizability was lower than that of the 4-O-branched disaccharide monomers reported previously, and the trisaccharide monomer was not polymerizable, probably due to the steric hindrance of the branched bulky mono and disaccharide units at the 3-O position in 1, 6-anhydro glucopyranose. Debenzylation of the resulting polymers gave 3-O-gluco-

  新的3-O支链1、6-脱水吡喃葡萄糖二糖单体，1，6-脱水-2、4-二-O-苄基-3-O-（2'，3'，4'，6'-四- O-苄基-α-D-甘露吡喃糖基）-（LGM 6）和-葡萄糖吡喃糖基）-β-D-吡喃葡萄糖（LGG 7）和三糖单体1、6-脱水-2、4-二-O-苄基-3-O-α-（2'，3'，6'，2''，3''，4''，6''-庚基-O-苄基-α-D-麦芽吡喃糖基）-β-D-吡喃葡萄糖（LGMAL 8 ）合成和聚合。发现3-O-支链的1，6-脱水二糖单体已聚合。然而，可聚合性低于先前报道的4-O-支化二糖单体，并且三糖单体不可聚合，这可能是由于1中3-O位置支链的庞大单糖和二糖单元的空间位阻，6-脱水吡喃葡萄糖。所得聚合物的脱苄基作用以中等收率得到了3-O-葡萄糖基和甘露吡喃糖苷（1→6）-α-D-吡喃葡聚糖。这些结果是3-O-支链的1,6-脱水脱水吡喃葡萄糖二糖单体聚合生成3-O-支链的多糖的首次报道。
• Synthesis of protected glucose derivatives from levoglucosan by development of common carbohydrate protecting group reactions under continuous flow conditions
  作者：Keevan C. Marion、Zachary Wooke、Nicola L.B. Pohl

  DOI：10.1016/j.carres.2018.08.002

  日期：2018.10

  Common carbohydrate protecting group reactions under continuous flow processes are reported in the context of producing partially-protected glucose building blocks from levoglucosan. Benzyl ether protection was demonstrated without the use of NaH using barium oxide, which, however, pointed to the need for forms of this catalyst not as susceptible to close packing under flow. Acylation conditions were

  在从左旋葡聚糖生产部分保护的葡萄糖结构单元的背景下，报道了在连续流动过程中常见的碳水化合物保护基反应。在不使用氧化钡的NaH的情况下证明了对苄醚的保护作用，然而，这表明需要这种催化剂的形式不易在流动条件下紧密堆积。在乙腈连续流动并避免吡啶的条件下开发了酰化条件。还证明了用丙硫醇对衍生的左旋葡聚糖进行开环可在2步而不是12步中产生S-烷基2,4-二-O-苄基-吡​​喃葡萄糖苷结构单元，从而提高总收率。
• Stereoselective synthesis of α-glycosyl azides by ring-opening of 1,6-anhydrosugars with trimethylsilyl azide
  作者：Tianyu Cui、Raymond Smith、Xiangming Zhu

  DOI：10.1016/j.carres.2015.08.002

  日期：2015.10

  We describe here an expedient and highly stereoselective procedure for the synthesis of alpha-glycosyl azides. Treatment of 1,6-anhydrosugars with trimethylsilyl azide in the presence of trimethylsilyl triflate led to the formation of alpha-glycosyl azides. All the reactions were highly stereoselective and afforded the alpha-glycosyl azides in good to excellent yields.

  我们在这里描述了一种方便且高度立体选择性的合成α-糖基叠氮化物的方法。在三甲基甲硅烷基三氟甲磺酸酯存在下用三甲基甲硅烷基叠氮化物处理1，6-脱水糖导致形成α-糖基叠氮化物。所有反应都是高度立体选择性的，并以良好至优异的产率提供了α-糖基叠氮化物。
• 1,6-anhydro-.beta.-hexopyranose derivatives and their use as herbicides
  申请人：Her Majesty the Queen in right of New Zealand

  公开号：US05047518A1

  公开（公告）日：1991-09-10

  Herbicidal and/or plant-growth regulatory compositions comprising, together with a carrier and/or surface-active agent, an effective amount of at least one herbicidal and/or plant growth regulatory active agent selected from compounds of formula (I) ##STR1## (in which R represents an optionally substituted aralkyl group, X represents an O--, N-- or S-linked organic group, an optionally substituted hydrocarbyl group, a halogen atom, a hydroxy, amino, alkoxyamino, nitro, cyano, azido, sulpho or phospho group, or together with the group R.sup.2e, X may represents a ketonic oxygen atom --O-- or a group of formula --CH.sub.2 O--; R.sup.1e represents a hydrogen atom or an optionally substituted hydrocarbyl group, or a formyl group; R.sup.2e represents a hydrogen atom, a hydroxy group or an optionally substituted hydrocarbyl or O-linked hydrocarbyl group, or, together with the group X, R.sup.2e may represent a ketonic oxygen atom --O-- or a group of formula --CH.sub.2 O--; R.sup.3a represents a hydrogen atom, a hydroxy group or an optionally substituted alkoxy, alkenyloxy, aralkoxy or C.sub.1-4 hydrocarbyl group; R.sup.3e represents a hydrogen atom, a hydroxy group or an optionally substituted hydrocarbyl or O-linked hydrocarbyl group; and R.sup.4e represents a hydrogen atom or an optionally substituted hydrocarbyl group) and enantiomers and salts thereof. Methods for preparing the compounds of formula (I) are described; the compositions are valuable as herbicides and/or plant-growth regulants, particularly for use with crops such as soya, rape, sugar-beet, cotton, wheat, maize and rice.

  含有除草剂和/或植物生长调节剂的组合物，与载体和/或表面活性剂一起，包括来自化合物的有效量至少一种除草剂和/或植物生长调节活性剂的选择(其中R代表可选择取代的芳基烷基基团，X代表与有机团相连的O-、N-或S-链的有机团，可选择取代的碳氢基团，卤素原子，羟基，氨基，烷氧基氨基，硝基，氰基，叠氮基，磺酰基或磷酰基团，或与基团R.sup.2e一起，X可以表示酮氧原子--O--或式--CH.sub.2 O--; R.sup.1e代表氢原子或可选择取代的碳氢基团，或甲酰基; R.sup.2e代表氢原子，羟基或可选择取代的碳氢基团或O-链的碳氢基团，或者与基团X一起，R.sup.2e可以表示酮氧原子--O--或式--CH.sub.2 O--; R.sup.3a代表氢原子，羟基或可选择取代的烷氧基，烯氧基，芳基氧基或C.sub.1-4碳氢基团; R.sup.3e代表氢原子，羟基或可选择取代的碳氢基团或O-链的碳氢基团; 和R.sup.4e代表氢原子或可选择取代的碳氢基团)及其对映体和盐。描述了制备式(I)化合物的方法；这些组合物对大豆、油菜、甜菜、棉花、小麦、玉米和稻米等作物的除草剂和/或植物生长调节剂特别有价值。