1-O-benzyl-α-D-glucofuranurono-6,3-lactone | 203632-50-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-benzyl-α-D-glucofuranurono-6,3-lactone
• 英文别名: 1-O-Benzyl-alpha-D-glucofuranurono-6,3-lactone；(2S,3R,3aR,6S,6aR)-3,6-dihydroxy-2-phenylmethoxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one
• CAS: 203632-50-2
• 化学式: C₁₃H₁₄O₆
• 分子量: 266.251
• InChiKey: HNIONWMHBLSOJK-KSLZLVKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-benzyl-α-D-glucofuranurono-6,3-lactone 在 palladium dihydroxide 吡啶 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 39.0h， 生成 2,5-di-O-acetyl-D-glucofuranurono-6,3-lactone
  参考文献：
  名称：

  Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones

  摘要：

  Alduronic acid 4,1-, 5,1-, and 5,2-lactones can be specifically obtained when hexuronic and penturonic acids belonging to the erythrose and threose carbohydrate series undergo a tandem beta-fragmentation-intramolecular cyclization reaction. In this way, gamma-lactones such as 3-O-formyl-1,2-O-isopropylidene-D-threurono-4,1-lactone (38), 3-O-formyl-1,2-di-O-methyl-D-threurono-4,1-lactones (39), or 3-O-formyl-1,2-O-isopropylidene-D-erythrurono-4,1-lactone (41), and delta-lactones such as 1-O-(tert-butyldimethylsilyl)-4-O-formyl-2,3-O-isopropylidene-D-lyxurono-5,1-lactones (40), or 4-O-formyl-1,2,3-tri-O-methyl-D-arabinurono-5,1-lactones (42), or 3-O-benzyl-4-O-formyl-1,2-O-isopropylidene-D-arabinurono-5,1-lactone (43), were obtained. Alternatively, an intermolecular reaction took place when the carboxyl group was lactonized. Thus, 1,4-di-O-acetyl-3-formyl-1-iodo-D-arabininurono-5,2-lactone (45) was prepared from 2,5-di-O-acetyl-D-glucurono-6,3-lactone (37). The reaction is promoted by two different systems: (diacetoxyiodo)benzene (DIB)-iodine, under mild conditions, or diphenylhydroxyselenium acetate (DHSA)-iodine under visible light irradiation. With this new strategy, nor-aldopyranosuronic and aldofuranosuronic acid lactones are formed via 1,5 and 1,6 intramolecular cyclization.

  DOI：

  10.1021/jo971323p
• 作为产物：
  描述：

  D-glucurono-6,3-lactone 、 苯甲醇 在 盐酸 作用下， 以 水 为溶剂， 反应 16.0h， 生成 1-O-benzyl-α-D-glucofuranurono-6,3-lactone
  参考文献：
  名称：

  GLUCURONOLACTONE DERIVATIVES AS SELF-TANNING SUBSTANCES

  摘要：

  该发明涉及将特定的葡萄糖醛内酯衍生物用作自我晒黑物质，用作增强二羟基丙酮的晒黑效果，或用于包含二羟基丙酮的自我晒黑物质混合物的调节，以调节使用二羟基丙酮或包含二羟基丙酮的混合物或制剂晒黑时所达到的颜色深浅，作为降低对比度的剂或用于给含角蛋白的纤维着色，以及用于含角蛋白纤维着色的制剂或组合物，其中包括这些特定的葡萄糖醛内酯衍生物。

  公开号：

  US20150098914A1

文献信息

• GLUCURONOLACTONDERIVATE ALS SELBSTBRÄUNUNGSSUBSTANZEN
  申请人：Merck Patent GmbH

  公开号：EP2787989B1

  公开（公告）日：2016-04-06
• US9649268B2
  申请人：——

  公开号：US9649268B2

  公开（公告）日：2017-05-16
• GLUCURONOLACTONE DERIVATIVES AS SELF-TANNING SUBSTANCES
  申请人：MERCK PATENT GMBH

  公开号：US20150098914A1

  公开（公告）日：2015-04-09

  The invention relates to the use of specific glucuronolactone derivatives as self-tanning substances, as tanning enhancers for dihydroxyacetone or for a mixture of self-tanning substances comprising dihydroxyacetone, for modulation of the colour shade achieved in the case of tanning with dihydroxyacetone or by the mixture or preparation comprising dihydroxyacetone, as contrast-reduction agents or for colouring keratin-containing fibres, and to preparations or compositions for colouring keratin-containing fibres comprising these specific glucuronolactone derivatives.

  该发明涉及将特定的葡萄糖醛内酯衍生物用作自我晒黑物质，用作增强二羟基丙酮的晒黑效果，或用于包含二羟基丙酮的自我晒黑物质混合物的调节，以调节使用二羟基丙酮或包含二羟基丙酮的混合物或制剂晒黑时所达到的颜色深浅，作为降低对比度的剂或用于给含角蛋白的纤维着色，以及用于含角蛋白纤维着色的制剂或组合物，其中包括这些特定的葡萄糖醛内酯衍生物。
• Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones
  作者：Cosme G. Francisco、Concepción González Martín、Ernesto Suárez

  DOI：10.1021/jo971323p

  日期：1998.4.1

  Alduronic acid 4,1-, 5,1-, and 5,2-lactones can be specifically obtained when hexuronic and penturonic acids belonging to the erythrose and threose carbohydrate series undergo a tandem beta-fragmentation-intramolecular cyclization reaction. In this way, gamma-lactones such as 3-O-formyl-1,2-O-isopropylidene-D-threurono-4,1-lactone (38), 3-O-formyl-1,2-di-O-methyl-D-threurono-4,1-lactones (39), or 3-O-formyl-1,2-O-isopropylidene-D-erythrurono-4,1-lactone (41), and delta-lactones such as 1-O-(tert-butyldimethylsilyl)-4-O-formyl-2,3-O-isopropylidene-D-lyxurono-5,1-lactones (40), or 4-O-formyl-1,2,3-tri-O-methyl-D-arabinurono-5,1-lactones (42), or 3-O-benzyl-4-O-formyl-1,2-O-isopropylidene-D-arabinurono-5,1-lactone (43), were obtained. Alternatively, an intermolecular reaction took place when the carboxyl group was lactonized. Thus, 1,4-di-O-acetyl-3-formyl-1-iodo-D-arabininurono-5,2-lactone (45) was prepared from 2,5-di-O-acetyl-D-glucurono-6,3-lactone (37). The reaction is promoted by two different systems: (diacetoxyiodo)benzene (DIB)-iodine, under mild conditions, or diphenylhydroxyselenium acetate (DHSA)-iodine under visible light irradiation. With this new strategy, nor-aldopyranosuronic and aldofuranosuronic acid lactones are formed via 1,5 and 1,6 intramolecular cyclization.