2,3,4,6-tetra-O-acetyl-L-glucoyranose | 188913-42-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-L-glucoyranose
• 英文别名: 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose；β-D-glucose-2,3,4,6-tetraacetate；[(2S,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-hydroxyoxan-2-yl]methyl acetate
• CAS: 188913-42-0
• 化学式: C₁₄H₂₀O₁₀
• 分子量: 348.307
• InChiKey: IEOLRPPTIGNUNP-HPCHECBXSA-N

物化性质

• 沸点：
  425.0±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-L-glucoyranose 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R)-4-hydroxy-7-methoxy-2-(2,3,4,6-tetra-O-acetyl-β-L-glucopyranosyloxy)-2H-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  Diastereoselective synthesis of the benzoxazinone acetal glucoside ent-GDIMBOA: the first enantiomer of a natural acetal glucoside

  摘要：

  The synthesis of (2S)-2-beta-L-glucopyranosyloxy-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, the enantiomer of the natural acetal glucoside GDIMBOA from maize, has been achieved by the double diastereoselective L-glucosylation of racemic 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one with 2,3,4,6-tetra-O-acetyl-beta-L-glucopyranosyl trichloroacetimidate in the presence of excess of boron trifluoride etherate as promoter as well as protecting and equilibrating agent. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00303-5
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide 在 silver carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以90%的产率得到2,3,4,6-tetra-O-acetyl-L-glucoyranose
  参考文献：
  名称：

  Diastereoselective synthesis of the benzoxazinone acetal glucoside ent-GDIMBOA: the first enantiomer of a natural acetal glucoside

  摘要：

  The synthesis of (2S)-2-beta-L-glucopyranosyloxy-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, the enantiomer of the natural acetal glucoside GDIMBOA from maize, has been achieved by the double diastereoselective L-glucosylation of racemic 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one with 2,3,4,6-tetra-O-acetyl-beta-L-glucopyranosyl trichloroacetimidate in the presence of excess of boron trifluoride etherate as promoter as well as protecting and equilibrating agent. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00303-5

文献信息

• Laccase-catalyzed dimerization of glycosylated lignols
  作者：Ivan Bassanini、Paolo Gavezzotti、Daniela Monti、Jana Krejzová、Vladimír Křen、Sergio Riva

  DOI：10.1016/j.molcatb.2016.10.019

  日期：2016.12

  Phenylpropanoid glucosides (PPGs) are naturally occurring and bioactive phenolic derivatives, largely distributed in plants. In this work different PPGs have been chemically or enzymatically synthesized from the lignols coniferyl and p-coumaryl alcohols as substrates for a lactase-catalyzed oxidative coupling. The biooxidation of these PPGs has been investigated here and novel dihydrobenzofuran-based structurally modified analogues have been isolated and characterized. Specifically, the presence of a carbohydrate moiety increased the water solubility of these compounds and reduced the number of dimeric products, as pinoresinol-like structures could not be formed. Looking for a possible sugar-promoted stereochemical enrichment of the obtained diastereomeric mixtures of dimers, different carbohydrate moieties (D-glucose, L-glucose and the disaccharide rutinose) were considered and the respective d.e. values of the dimeric products were measured by H-1 NMR and HPLC. However, it was found that the sugar substituent had a minor effect on the stereochemical outcome of the radical coupling reactions, the best measured result being a d.e. value of 21%. (C) 2016 Elsevier B.V. All rights reserved.
• Photo‐Excited Nickel‐Catalyzed Silyl‐Radical‐Mediated Direct Activation of Carbamoyl Chlorides To Access (Hetero)aryl Carbamides**
  作者：Sudip Maiti、Sayan Roy、Pintu Ghosh、Aashi Kasera、Debabrata Maiti

  DOI：10.1002/anie.202207472

  日期：2022.11.2

  AbstractAmide bonds connect the amino acids in proteins and exist as a prevalent structural motif in biomolecules. Herein, we have exploited the concept of cross‐electrophile coupling by merging the photo‐redox and transition‐metal catalysis to construct carbamides from superabundant (hetero)aryl halides along with commercially feasible carbamoyl chlorides. The success of this method relies on the prior formation of NiII‐aryl halide intermediates, which involves in a photoexcited Ni‐halide homolysis event by energy transfer from aryl bromide and single‐electron transfer from aryl chloride to assist generation of the vital carbamoyl radical. The breadth of application of this technique is demonstrated both in inter‐ as well as intramolecular routes for the synthesis of a plethora of (hetero)aryl carbamides with diverse functionalities, and biologically important benzolactams.
• Yadava, Virenda Singh; Misra, Krishna, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 875 - 877
  作者：Yadava, Virenda Singh、Misra, Krishna

  DOI：——

  日期：——
• Diastereoselective synthesis of the benzoxazinone acetal glucoside ent-GDIMBOA: the first enantiomer of a natural acetal glucoside
  作者：Michael Kluge、Bernd Schneider、Dieter Sicker

  DOI：10.1016/s0008-6215(96)00303-5

  日期：1997.3

  The synthesis of (2S)-2-beta-L-glucopyranosyloxy-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, the enantiomer of the natural acetal glucoside GDIMBOA from maize, has been achieved by the double diastereoselective L-glucosylation of racemic 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one with 2,3,4,6-tetra-O-acetyl-beta-L-glucopyranosyl trichloroacetimidate in the presence of excess of boron trifluoride etherate as promoter as well as protecting and equilibrating agent. (C) 1997 Elsevier Science Ltd.