(S)-3-(benzyloxy)-5-((R)-1,2-dihydroxyethyl)furan-2(5H)-one | 55123-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (S)-3-(benzyloxy)-5-((R)-1,2-dihydroxyethyl)furan-2(5H)-one
• 英文别名: (2S)-2-[(1R)-1,2-dihydroxyethyl]-4-phenylmethoxy-2H-furan-5-one
• CAS: 55123-48-3
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: JYMMLFUENKIMOU-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(benzyloxy)-5-((R)-1,2-dihydroxyethyl)furan-2(5H)-one 在 palladium on activated charcoal 环己烯 作用下， 以 甲醇 为溶剂， 以100%的产率得到(2S)-2-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2H-furan-5-one
  参考文献：
  名称：

  A two step synthesis of 3-deoxy-d- or l-glycono-1,4-lactones and 2-0-alkyl-3-deoxy-d-glycono-1,4-lactones from d- or l-glyconolactones

  摘要：

  Treatment of unprotected D-or L-glyconolactones with sodium hydride and alkyl halides, in dimethylsulfoxide, led to the corresponding 2-O-alkyl-3-deoxy-2-enono-1,4-lactones. Hydrogenolysis of 2-O-benzyl derivatives by catalytic hydrogen transfer with palladium on charcoal and cyclohexene as hydrogen donor gave 3-deoxy-hex- or pent-2-enono-1,4-lactones in the enolic forms. Reduction of 2-O-benzyl-enonolactones with ammonium formate as hydrogen donor afforded 3-deoxy-D- or L-glycono-1,4-lactones when 2-O-alkyl ethers gave the corresponding ethers. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00164-x
• 作为产物：
  描述：

  溴甲苯 、 葡萄糖酸内酯 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 以26%的产率得到(S)-3-(benzyloxy)-5-((R)-1,2-dihydroxyethyl)furan-2(5H)-one
  参考文献：
  名称：

  ASCORBIC ACID-RELATED COMPOUND AND ANTI-PLANT-VIRUS AGENT

  摘要：

  本发明提供一种由式（1）表示的化合物（其中X1和X2中的每一个独立表示-OR1、-NR2R3或-CR4R5R6等，R1、R2、R3、R4、R5和R6中的每一个独立表示未取代或取代基团的糖基或未取代或取代基团的C1至C30烷基基团等，A表示未取代或取代基团的C1至C30烷基基团等）或其盐。

  公开号：

  EP2902387A1

文献信息

• ASCORBIC ACID-RELATED COMPOUND AND PLANT ANTIVIRAL AGENT
  申请人：NIPPON SODA CO., LTD.

  公开号：US20150250169A1

  公开（公告）日：2015-09-10

  The present invention provides a compound represented by formula (1) (wherein each of X 1 and X 2 independently represents —OR 1 , —NR 2 R 3 or —CR 4 R 5 R 6 or the like, each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represents an unsubstituted or substituent-bearing glycosyl group or an unsubstituted or substituent-bearing C1 to C30 alkyl group or the like, and A represents an unsubstituted or substituent-bearing C1 to C30 alkyl group or the like) or a salt thereof.

  本发明提供一种由式（1）表示的化合物（其中X1和X2分别独立表示—OR1，—NR2R3或—CR4R5R6或类似物，R1、R2、R3、R4、R5和R6分别独立表示未取代或取代基的糖基或未取代或取代基的C1到C30烷基或类似物，A表示未取代或取代基的C1到C30烷基或类似物）或其盐。
• ASCORBIC ACID-RELATED COMPOUND AND ANTI-PLANT-VIRUS AGENT
  申请人：Nippon Soda Co., Ltd.

  公开号：EP2902387A1

  公开（公告）日：2015-08-05

  The present invention provides a compound represented by formula (1) (wherein each of X1 and X2 independently represents -OR1, -NR2R3 or -CR4R5R6 or the like, each of R1, R2, R3, R4, R5 and R6 independently represents an unsubstituted or substituent-bearing glycosyl group or an unsubstituted or substituent-bearing C1 to C30 alkyl group or the like, and A represents an unsubstituted or substituent-bearing C1 to C30 alkyl group or the like) or a salt thereof.

  本发明提供一种由式（1）表示的化合物（其中X1和X2中的每一个独立表示-OR1、-NR2R3或-CR4R5R6等，R1、R2、R3、R4、R5和R6中的每一个独立表示未取代或取代基团的糖基或未取代或取代基团的C1至C30烷基基团等，A表示未取代或取代基团的C1至C30烷基基团等）或其盐。
• A two step synthesis of 3-deoxy-d- or l-glycono-1,4-lactones and 2-0-alkyl-3-deoxy-d-glycono-1,4-lactones from d- or l-glyconolactones
  作者：Caroline Choquet-Farnier、Imane Stasik、Daniel Beaupère

  DOI：10.1016/s0008-6215(97)00164-x

  日期：1997.9

  Treatment of unprotected D-or L-glyconolactones with sodium hydride and alkyl halides, in dimethylsulfoxide, led to the corresponding 2-O-alkyl-3-deoxy-2-enono-1,4-lactones. Hydrogenolysis of 2-O-benzyl derivatives by catalytic hydrogen transfer with palladium on charcoal and cyclohexene as hydrogen donor gave 3-deoxy-hex- or pent-2-enono-1,4-lactones in the enolic forms. Reduction of 2-O-benzyl-enonolactones with ammonium formate as hydrogen donor afforded 3-deoxy-D- or L-glycono-1,4-lactones when 2-O-alkyl ethers gave the corresponding ethers. (C) 1997 Elsevier Science Ltd.