(-)-1-O-β-D-glucopyranosyloxy-3-methyl-2-buten-1-ol | 117861-55-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (-)-1-O-β-D-glucopyranosyloxy-3-methyl-2-buten-1-ol
• 英文别名: 1-O-β-D-glucopyranosyloxy-3-methylbut-2-en；3-methyl-but-2-en-1-yl β-D-glucopyranoside；3-methyl-but-2-en-1-yl-β-D-glucopyranoside；3-methyl-2-buten-1-ol β-D-glucopyranoside；3-methyl-2-butenyl β-D-glucopyranoside；prenyl glucoside；beta-D-Glucopyranoside, 3-methyl-2-buten-1-yl；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(3-methylbut-2-enoxy)oxane-3,4,5-triol
• CAS: 117861-55-9
• 化学式: C₁₁H₂₀O₆
• 分子量: 248.276
• InChiKey: GQJQCKUJCHMTNF-KAMPLNKDSA-N

物化性质

• 熔点：
  78-81 °C
• 沸点：
  433.9±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-1-O-β-D-glucopyranosyloxy-3-methyl-2-buten-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 二甲基硫 、 臭氧 作用下， 反应 2.75h， 生成 2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyl)ethanal
  参考文献：
  名称：

  Chemoenzymatic syntheses of naturally occurring β-glucosides

  摘要：

  Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4-nitrophenyl-beta-D-glucopyranoside 4 using beta-glucosidase from almonds gave stereoselectively beta-D-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring beta-glucosides in moderate yield. Among them, the beta-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00228-1
• 作为产物：
  描述：

  纤维素二糖 、 异戊烯醇 在 Pyrococcus furiosus β-glucosidase/gelatin-gel 作用下， 反应 12.0h， 以26%的产率得到(-)-1-O-β-D-glucopyranosyloxy-3-methyl-2-buten-1-ol
  参考文献：
  名称：

  Synthesis of Alkyl β -Glucosides by Transglucosylation Using Pyrococcus furiosus β -Glucosidase Immobilized onto Gelatin Gel

  摘要：

  合成烷基 β-吡喃葡萄糖苷，如对甲氧基苯甲酰 β-D-吡喃葡萄糖苷、苯乙基 β-D-吡喃葡萄糖苷、水杨梅苷、肉桂基 β-D-吡喃葡萄糖苷、柑橘苷 D、3-甲基丁基 β-D-吡喃葡萄糖苷、3-甲基-2-丁烯基 β-D-吡喃葡萄糖苷、使用固定在明胶凝胶上的超恒温 Pyrocmostable Furiosus β-葡萄糖苷酶，以中等产量完成了β-D-吡喃葡萄糖苷、香叶基 β-D-吡喃葡萄糖苷、紫苏糖苷 A 和环己基 β-D-吡喃葡萄糖苷的转葡糖基化。回收的固定化物可在连续的反式葡萄糖基化过程中重复使用。

  DOI：

  10.2174/157017809787582762

文献信息

• Ackermann, Irmtraud E.; Banthorpe, Derek V.; Fordham, William D., Liebigs Annalen der Chemie, 1989, p. 79 - 82
  作者：Ackermann, Irmtraud E.、Banthorpe, Derek V.、Fordham, William D.、Kinder, John P.、Poots, Ian

  DOI：——

  日期：——
• ACKERMANN, IRMTRAUD E.;BANTHORPE, DEREK V.;FORDHAM, WILLIAM D.;KINDER, JO+, LIEBIGS ANN. CHEM.,(1989) N, C. 79-81
  作者：ACKERMANN, IRMTRAUD E.、BANTHORPE, DEREK V.、FORDHAM, WILLIAM D.、KINDER, JO+

  DOI：——

  日期：——
• Chemoenzymatic syntheses of naturally occurring β-glucosides
  作者：Hiroyuki Akita、Katsumi Kurashima、Takuya Nakamura、Keisuke Kato

  DOI：10.1016/s0957-4166(99)00228-1

  日期：1999.6

  Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4-nitrophenyl-beta-D-glucopyranoside 4 using beta-glucosidase from almonds gave stereoselectively beta-D-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring beta-glucosides in moderate yield. Among them, the beta-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of Alkyl β -Glucosides by Transglucosylation Using Pyrococcus furiosus β -Glucosidase Immobilized onto Gelatin Gel
  作者：Yoh-ichi Matsushita、Hidetaka Nagatomo、Kazuhiro Sugamoto、Takanao Matsui

  DOI：10.2174/157017809787582762

  日期：2009.3.1

  Synthesis of alkyl β-glucosides such as p-anisyl β-D-glucopyranoside, phenethyl β-D-glucopyranoside, salidroside, cinnamyl β-D-glucopyranoside, citrusin D, 3-methylbutyl β-D-glucopyranoside, 3-methyl-2-butenyl β-Dglucopyranoside, geranyl β-D-glucopyranoside, perilloside A, and cyclohexyl β-D-glucopyranoside was accomplished in moderate yields by transglucosylation using hyperthermostable Pyrococcus furiosus β-glucosidase immobilized onto gelatin gel. Recovered immobilisate was reusable on successive runs in transglucosylation.

  合成烷基 β-吡喃葡萄糖苷，如对甲氧基苯甲酰 β-D-吡喃葡萄糖苷、苯乙基 β-D-吡喃葡萄糖苷、水杨梅苷、肉桂基 β-D-吡喃葡萄糖苷、柑橘苷 D、3-甲基丁基 β-D-吡喃葡萄糖苷、3-甲基-2-丁烯基 β-D-吡喃葡萄糖苷、使用固定在明胶凝胶上的超恒温 Pyrocmostable Furiosus β-葡萄糖苷酶，以中等产量完成了β-D-吡喃葡萄糖苷、香叶基 β-D-吡喃葡萄糖苷、紫苏糖苷 A 和环己基 β-D-吡喃葡萄糖苷的转葡糖基化。回收的固定化物可在连续的反式葡萄糖基化过程中重复使用。