1,3,4,5,7-penta-O-acetyl-2,6-anhydro-L-glycero-L-galacto-heptitol | 115224-88-9

• 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: 1,3,4,5,7-penta-O-acetyl-2,6-anhydro-L-glycero-L-galacto-heptitol
• 英文别名: 1,3,4,5,7-Penta-O-acetyl-2,6-Anhydro-D-glycero-L-manno-heptotol
• CAS: 115224-88-9
• 化学式: C₁₇H₂₄O₁₁
• 分子量: 404.371
• InChiKey: NSESSVVOVAHLTQ-BQJWPVKWSA-N

物化性质

• 沸点：
  453.0±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1,3,4,5,7-penta-O-acetyl-2,6-anhydro-L-glycero-L-galacto-heptitol 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium azide 、 sodium methylate 、 对甲苯磺酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 2,6-anhydro-4-azido-1,3:5,7-di-O-benzylidene-4-deoxy-L-glycero-L-gluco-heptitol
  参考文献：
  名称：

  Synthesis studies of structural analogues of tagetitoxin: 2-phosphate

  摘要：

  Synthetic approaches to structural analogues of tagetitoxin (1) are described. The successful route to analogue 3 (X=O) has, as a key step, protection of the cis-vicinal amino alcohol moiety of compound 7 as an N-benzylated cyclic carbamate (9). X-Ray crystallographic analyses of the hydrochloride of compound 7 and of the hydroxyacid 56 are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00327-0
• 作为产物：
  描述：

  (2R,3S,4R,5S,6S)-2-(乙酰氧基甲基)-6-氰基四氢-2H-吡喃-3,4,5-三基三乙酸酯 在 镍 吡啶 、 sodium tetrahydroborate 、 sodium hypophosphite 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 0.66h， 生成 1,3,4,5,7-penta-O-acetyl-2,6-anhydro-L-glycero-L-galacto-heptitol
  参考文献：
  名称：

  Synthesis studies of structural analogues of tagetitoxin: 2-phosphate

  摘要：

  Synthetic approaches to structural analogues of tagetitoxin (1) are described. The successful route to analogue 3 (X=O) has, as a key step, protection of the cis-vicinal amino alcohol moiety of compound 7 as an N-benzylated cyclic carbamate (9). X-Ray crystallographic analyses of the hydrochloride of compound 7 and of the hydroxyacid 56 are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00327-0

文献信息

• Coupling of anhydro-aldose tosylhydrazones with hydroxy compounds and carboxylic acids: a new route for the synthesis of C-β-<scp>d</scp>-glycopyranosylmethyl ethers and esters
  作者：Tímea Kaszás、Marietta Tóth、Sándor Kun、László Somsák

  DOI：10.1039/c6ra27282g

  日期：——

  tosylhydrazones) with alcohols, phenols, and carboxylic acids were studied under thermic or photolytic conditions in the presence of K3PO4 or LiOtBu. The reactions failed with EtOH, BnOH, or tBuOH, however, (CF3)2CHOH, electron poor phenols and carboxylic acids gave the corresponding C-β-D-glycopyranosylmethyl ethers and esters, respectively, representing a new access to these glycomimetic compounds.

  在K 3 PO 4存在下，在热或光解条件下研究了O-过酰化的2，6-脱水醛糖甲苯磺酰yl（C-（β- D-甘露糖基）甲醛甲苯磺酰to）与醇，酚和羧酸的交叉偶联。或LiO t Bu。用EtOH，BnOH或t BuOH可使反应失败，但是，（CF 3）2 CHOH，电子贫乏的酚和羧酸分别产生相应的C- β- D-糖基核糖基甲基醚和酯，代表了使用这些糖模拟物的新途径化合物。
• Catalytic siloxymethylation of glycosides by the HSiR3/CO/CO2(CO)8 reaction. A new entry to C-glycosyl compounds
  作者：Naoto Chatani、Toshihiro Ikeda、Takahiro Sano、Noboru Sonoda、Hideo Kurosawa、Yoshikane Kawasaki、Shinji Murai

  DOI：10.1021/jo00249a059

  日期：1988.7
• CHATANI, N.;IREDA, T.;SANO, T.;SONODA, N.;KUROSAWA, H.;KAWASAKI, Y.;MURAI+, J. ORG. CHEM., 53,(1988) N 14, 3387-3389
  作者：CHATANI, N.、IREDA, T.、SANO, T.、SONODA, N.、KUROSAWA, H.、KAWASAKI, Y.、MURAI+

  DOI：——

  日期：——
• Synthesis studies of structural analogues of tagetitoxin: 2-phosphate
  作者：Barry R. Dent、Richard H. Furneaux、Graeme J. Gainsford、Gregory P. Lynch

  DOI：10.1016/s0040-4020(99)00327-0

  日期：1999.5

  Synthetic approaches to structural analogues of tagetitoxin (1) are described. The successful route to analogue 3 (X=O) has, as a key step, protection of the cis-vicinal amino alcohol moiety of compound 7 as an N-benzylated cyclic carbamate (9). X-Ray crystallographic analyses of the hydrochloride of compound 7 and of the hydroxyacid 56 are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.