3-(4'-O-acetyl-2',3',6'-trideoxy-β-L-erythro-hex-2'-enopyranosyl)-1-propene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-(4'-O-acetyl-2',3',6'-trideoxy-β-L-erythro-hex-2'-enopyranosyl)-1-propene
• 英文别名: [(2S,3R,6R)-2-methyl-6-prop-2-enyl-3,6-dihydro-2H-pyran-3-yl] acetate
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: YYQUYDARQNUCRP-JMJZKYOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 、 烯丙基三甲基硅烷 在 erbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-(4'-O-acetyl-2',3',6'-trideoxy-β-L-erythro-hex-2'-enopyranosyl)-1-propene 、 3-(4'-O-acetyl-2',3',6'-trideoxy-α-L-erythro-hex-2'-enopyranosyl)-1-propene
  参考文献：
  名称：

  Er(OTf)₃as New Efficient Catalyst for the Stereoselective Synthesis ofC-Pseudoglycals

  摘要：

  Er(OTf)3是一种有效的催化剂，可用于Ferrier重排反应，提供高产率的产物，反应过程更清洁，反应时间短，反应条件温和，立体选择性高，催化剂可回收，且也可商业获得。

  DOI：

  10.1055/s-2005-918504

文献信息

• Environmentally compatible C-glycosidation of glycals using montmorillonite K-10
  作者：Kazunobu Toshima、Naoki Miyamoto、Goh Matsuo、Masaya Nakata、Shuichi Matsumura

  DOI：10.1039/cc9960001379

  日期：——

  The C-glycosidations of glycal acetates 1–4 with allyltrimethylsilane 5, vinyloxytrimethylsilane 6 or isopropenyl acetate 7 using montmorillonite K-10 as an environmentally acceptable and inexpensive industrial catalyst under mild conditions proceed effectively to give the corresponding 2,3-unsaturated C-glycosides in high yields.

  甘油醛乙酸酯1-4在温和条件下，以蒙脱土K-10作为环境友好且经济的工业催化剂，与烯丙基三甲基硅烷5、乙烯氧基三甲基硅烷6或异丙烯基乙酸酯7进行C-糖基化反应，高效地生成了相应的2,3-不饱和C-糖苷，产率极高。
• LiBF4-mediated C-glycosylation of glycals with allyltrimethylsilane: a facile synthesis of allyl C-glycosylic compounds
  作者：Jhillu S Yadav、Basi V.Subba Reddy、Lagisetti Chandraiah、Katham Srinivasa Reddy

  DOI：10.1016/s0008-6215(01)00087-8

  日期：2001.5

  The treatment of glycals with allyltrimethylsilane in the presence of lithium tetrafluoroborate in acetonitrile gave the corresponding allyl 2,3-unsaturated C-glycosylic compounds in excellent yields with high anomeric selectivity.

  在四氟硼酸锂在乙腈中存在的条件下，用烯丙基三甲基硅烷处理糖基得到了相应的烯丙基2,3-不饱和C-糖基化合物，具有优异的收率和高的异头选择性。
• Allyl C-glycosidations of totally unprotected glycals and allyltrimethylsilane with trimethylsilyl trifluoromethanesulfonate (TMSOTf)
  作者：Kazunobu Toshima、Toru Ishizuka、Goh Matsuo、Masaya Nakata

  DOI：10.1016/s0040-4039(00)77276-5

  日期：1994.8

  Allyl C-glycosidations of the totally unprotected glycals, L-rhamnal (1), D-glucal (2), D-galactal (3) and D-fucal (4), with allyltrimethylsilane (5) using TMSOTf proceeded much more effectively than those of the corresponding acetylated glycals 10∼13 to furnish the unprotected and 2,3-unsaturated allyl α-C-glycosides 6∼9 in high yields, respectively.

  烯丙基Ç的完全未保护的烯糖的-glycosidations，L-rhamnal（1），d-己烯糖（2），d半乳醛（3）和d-fucal（4）中，用烯丙基三甲基硅烷（5使用将TMSOTf）进行更有力的它们分别以相应的乙酰化糖基10-13的残基高收率提供未保护的和2，3-不饱和烯丙基α- C-糖苷6-9。
• Aryl and Allyl <i>C</i>-Glycosidation Methods Using Unprotected Sugars
  作者：Kazunobu Toshima、Goh Matsuo、Toru Ishizuka、Yasunobu Ushiki、Masaya Nakata、Shuichi Matsumura

  DOI：10.1021/jo972146v

  日期：1998.4.1

  Practical and highly stereoselective aryl and allyl C-glycosidation methods using unprotected sugars as glycosyl donors have been developed. Aryl C-glycosidations of several unprotected 2-deoxy sugars with phenol and naphthol derivatives by the combined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf)-AgClO4 or TMSOTf exclusively gave the corresponding unprotected o-hydroxyaryl beta-C-glycosides which appear in many biologically attractive aryl C-glycoside antibiotics as the key subunit. On the other hand, allyl C-glycosidations of several unprotected glycals with allyltrimethylsilane by TMSOTf afforded the corresponding unprotected and 2,3-unsaturated allyl alpha-C-glycosides in high yields which are versatile synthetic intermediates for the syntheses of optically active natural products.
• Microwave-induced, InCl3-catalyzed Ferrier rearrangement of acetylglycals: synthesis of 2,3-unsaturated C-glycosides
  作者：Saibal Kumar Das、K.Anantha Reddy、Chandrasekhar Abbineni、Joyita Roy、K.V.L.Narasimha Rao、Rachna H. Sachwani、Javed Iqbal

  DOI：10.1016/s0040-4039(03)01012-8

  日期：2003.6

  Indium(III) chloride-catalyzed, microwave-assisted Ferrier rearrangement of different per-O-acetylglycals leads to all efficient synthesis of 2.3-unsaturated C-glycosides in good to excellent yields. (C) 2003 Elsevier Science Ltd. All rights reserved.