1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol | 137035-64-4

• 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: 1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol
• 英文别名: 4-O-Benzyl-L-fucal；(2S,3R,4S)-2-methyl-4-phenylmethoxy-3,4-dihydro-2H-pyran-3-ol
• CAS: 137035-64-4
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: HDSJWJXPMACIGC-WCFLWFBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol 在 吡啶 、 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 72.0h， 生成 benzyl 3-azido-(3-O-benzyl-2,6-dideoxy-2-iodo-α-L-talopyranosyl)-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside
  参考文献：
  名称：

  Approaches to the C-B-A trisaccharide of dihydroaclacinomycin by extending the chain from either side

  摘要：

  Selective benzylation of L-fucal (1) under phase-transfer conditions gave the 3- and 4-monoethers 2 and 3, respectively. Two routes, the "tail" or the "head" addition are presented, both leading to the target molecule 9, a mimic of the C-B-A trisaccharide component of dihydroaclacinomycin. Addition of glycals 2 and 3 respectively, to the acetylated glycal (7) of amicetose used as glycosyl donor gave the disaccharide glycals 6 and 8. Alternatively, glucosylation of the 4-acetate (4) of 2 with the benzyl hex-2-enopyranoside derivative 10 gave the disaccharide derivative 11. In the first case, the final glycosylation step involves the addition of 10 to disaccharide glycal 8. In the second procedure, the disaccharide alcohol 12 is obtained by O-deacetylation of 11, and serves as the glycosyl acceptor for glycal derivative 7 to give the C-B-a precursor trisaccharide derivative.

  DOI：

  10.1016/0008-6215(92)84182-r
• 作为产物：
  描述：

  溴甲苯 、 L-fucal 在 氢氧化钾 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以19%的产率得到1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol
  参考文献：
  名称：

  Approaches to the C-B-A trisaccharide of dihydroaclacinomycin by extending the chain from either side

  摘要：

  Selective benzylation of L-fucal (1) under phase-transfer conditions gave the 3- and 4-monoethers 2 and 3, respectively. Two routes, the "tail" or the "head" addition are presented, both leading to the target molecule 9, a mimic of the C-B-A trisaccharide component of dihydroaclacinomycin. Addition of glycals 2 and 3 respectively, to the acetylated glycal (7) of amicetose used as glycosyl donor gave the disaccharide glycals 6 and 8. Alternatively, glucosylation of the 4-acetate (4) of 2 with the benzyl hex-2-enopyranoside derivative 10 gave the disaccharide derivative 11. In the first case, the final glycosylation step involves the addition of 10 to disaccharide glycal 8. In the second procedure, the disaccharide alcohol 12 is obtained by O-deacetylation of 11, and serves as the glycosyl acceptor for glycal derivative 7 to give the C-B-a precursor trisaccharide derivative.

  DOI：

  10.1016/0008-6215(92)84182-r

文献信息

• MACROCYCLIC PICOLINAMIDES AS FUNGICIDES
  申请人：DOW AGROSCIENCES LLC

  公开号：US20130296375A1

  公开（公告）日：2013-11-07

  The invention relates to macrocyclic picolinamides of Formula I and their use as fungicides.

  这项发明涉及式I的大环状吡啶甲酰胺及其作为杀菌剂的应用。
• US20140275171A1
  申请人：——

  公开号：US20140275171A1

  公开（公告）日：2014-09-18
• US8785479B2
  申请人：——

  公开号：US8785479B2

  公开（公告）日：2014-07-22
• US9144239B2
  申请人：——

  公开号：US9144239B2

  公开（公告）日：2015-09-29
• [EN] MACROCYCLIC PICOLINAMIDES AS FUNGICIDES<br/>[FR] PICOLINAMIDES MACROCYCLIQUES EN TANT QUE FONGICIDES
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2013169662A2

  公开（公告）日：2013-11-14

  The invention relates to macrocyclic picolinamides of Formula (I) and their use as fungicides.