2,3,4,6-四-O-乙酰基亚麻苦苷 | 66432-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,3,4,6-四-O-乙酰基亚麻苦苷
• 英文名称: 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)isobutyronitrile
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-cyanopropan-2-yloxy)oxan-2-yl]methyl acetate
• CAS: 66432-53-9
• 化学式: C₁₈H₂₅NO₁₀
• 分子量: 415.397
• InChiKey: LKTQBMQWABNFQQ-UUAJXVIYSA-N

物化性质

• 熔点：
  140-141°C
• 沸点：
  484.4±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四-O-乙酰基亚麻苦苷 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以80%的产率得到菜豆苷
  参考文献：
  名称：

  Facile Synthesis of Cyanogen Glycosides (R)-Prunasin, Linamarin and (S)-Heterodendrin.

  摘要：

  通过糖基化、羧酰胺脱水形成氰醇以及脱保护的三步反应，描述了从 O-(2,3,4,6-O-四乙酰基-α-D-吡喃葡萄糖基)三氯噻嗪酸和相应的 α-羟基酰胺合成氰苷（R）-普鲁纳辛、亚麻酰胺和（S）-heterodendrin 的简便合成路线。

  DOI：

  10.1271/bbb.62.453
• 作为产物：
  描述：

  2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 在 草酰氯 、 三氟化硼乙醚 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.42h， 生成 2,3,4,6-四-O-乙酰基亚麻苦苷
  参考文献：
  名称：

  Facile Synthesis of Cyanogen Glycosides (R)-Prunasin, Linamarin and (S)-Heterodendrin.

  摘要：

  通过糖基化、羧酰胺脱水形成氰醇以及脱保护的三步反应，描述了从 O-(2,3,4,6-O-四乙酰基-α-D-吡喃葡萄糖基)三氯噻嗪酸和相应的 α-羟基酰胺合成氰苷（R）-普鲁纳辛、亚麻酰胺和（S）-heterodendrin 的简便合成路线。

  DOI：

  10.1271/bbb.62.453

文献信息

• Cyanohydrin glycosides of passifloraceae☆
  作者：Elin S. Olafsdottir、Jan Vanggaard Andersen、Jerzy W. Jaroszewski

  DOI：10.1016/0031-9422(89)85023-x

  日期：——

  cyclopentenoid cyanohydrin glucoside, was shown to be (1S,4S)-1-(β- d -glucopyranosyloxy)-4-hydroxy-2-cyclopentene-1-carbonitrile, being thus identical with tetraphyllin B, contrary to previous statements in the literature. Cyanohydrin glycosides from Adenia dinklagei, A. epigea, A. firingalavensis, A. frutescens, A. hastata, A. letouzeyi, A. spinosa, Passiflora coriacea, P. subpeltata, P. warmingii and Smeathmannia

  摘要 Barterin 是一种经典的环戊烯类氰醇葡萄糖苷，被证明是 (1S,4S)-1-(β-d -glupyranosyloxy)-4-hydroxy-2-cyclopentene-1-carbonitrile，因此与四叶素 B 相同，与以前文献中的陈述。从 Adenia dinklagei、A.epigea、A.firealavensis、A.frutescens、A. hastata、A.letouzeyi、A. spinosa、Passiflora coriacea、P. subpeltata、P.warmii 和 Smeathmannia pubescens 中分离并鉴定了氰醇苷。对西番莲科中氰醇糖苷分布的现有知识的总结表明，两个主要属 Adenia 和 Passiflora 之间存在明显差异。因此，前一属似乎以 2-环戊烯-1-酮和 4-羟基-2-环戊烯-1-酮氰醇的 β-d-
• Cyanogenic and non-cyanogenic glycosides from Manihot esculenta
  作者：Hunsa Prawat、Chulabhorn Mahidol、Somsak Ruchirawat、Uma Prawat、Pittaya Tuntiwachwuttikul、Uncharee Tooptakong、Waltor C. Taylor、Chaveng Pakawatchai、Brian W. Skelton、Allen H. White

  DOI：10.1016/0031-9422(95)00398-q

  日期：1995.11

  In addition to lotaustralin and linamarin, a novel cyanogenic glycoside, 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)-2-methylbutanenitrile two novel non-cyanogenic glycosides, (2S)-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)butane and 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)propane, and a simple non-cyanogenic glycoside, ethyl beta-D-glucopyranoside, were isolated from an ethanolic extract of the fresh root cortex of Manihot esculenta. From a methanolic extract of the fresh leaves of this species lotaustralin and linamarin, and two flavonoid glycosides, kaempferol-3-O-rutinoside and quercetin-3-O-rutinoside were isolated.
• Activated dimethyl sulfoxide dehydration of amide and its application to one-pot preparation of benzyl-type perfluoroimidates
  作者：Noriyuki Nakajima、Miho Saito、Makoto Ubukata

  DOI：10.1016/s0040-4020(02)00304-6

  日期：2002.4

  Various types of primary amides were treated under an activated dimethyl sulfoxide (DMSO) species, (COCl)(2)-DMSO and Et3N, as a dehydrating agent to obtain nitriles in excellent yield. This dehydration system was extended to a one-pot preparation of perfluoroimidates via volatile perfluoronitriles from perfluoroamides. Fifteen benzyl-type perfluoroimidates can be prepared in 70-90% yield as more stable imidates than the trichloro analogue. MPM- and DMPM-perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Anam, Edet M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 3, p. 423 - 429
  作者：Anam, Edet M.

  DOI：——

  日期：——
• Facile Synthesis of Cyanogen Glycosides (R)-Prunasin, Linamarin and (S)-Heterodendrin.
  作者：Noriyuki NAKAJIMA、Makoto UBUKATA

  DOI：10.1271/bbb.62.453

  日期：——

  A facile synthetic route is described to cyanogenic glycosides (R)-prunasin, linamarin and (S)-heterodendrin from O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)trichloroace- timidate and the corresponding α-hydroxyamides by a 3-step reaction of glycosylation, cyanohydrin formation by dehydration of carboxamides, and deprotection.

  通过糖基化、羧酰胺脱水形成氰醇以及脱保护的三步反应，描述了从 O-(2,3,4,6-O-四乙酰基-α-D-吡喃葡萄糖基)三氯噻嗪酸和相应的 α-羟基酰胺合成氰苷（R）-普鲁纳辛、亚麻酰胺和（S）-heterodendrin 的简便合成路线。