(2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[3-(4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol | 62512-26-9

• 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: (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[3-(4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol
• 英文别名: 3-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-1-methyl-2-propyn-1-yl I(2)-D-glucopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[4-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)but-3-yn-2-yloxy]oxane-3,4,5-triol
• CAS: 62512-26-9
• 化学式: C₁₉H₃₀O₇
• 分子量: 370.443
• InChiKey: NVFMDEVKKYQMLD-KWEBYEANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[3-(4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol 在 吡啶 作用下， 生成 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-(4-acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of Glucosides Related to Grape and Wine Aroma Precursors

  摘要：

  Syntheses of the following glucosides are reported: 3',5',5'-trimethyl-3'-cyclohexenyl beta-D-glucopyranoside, 3'-(1 ''-cyclohexenyl)-1'-methyl-2'-propynyl-beta-D-glucopyranoside, (3'R*,9'S*)-3'-hydroxy-5'-megastigmen-7'-yn-9'-yl beta-D-glucopyranoside, (E,3'R*)-7'-oxo-5',8'-megastigmadien-3'-yl beta-D-glucopyranoside, and 4'-oxo-5'-megastigmen-9'-yl beta-D-glucopyranoside.

  DOI：

  10.1021/jf00052a025
• 作为产物：
  描述：

  (3'R^*,9'S^*)-3'-hydroxy-5'-megastigmen-7'-yn-9'-yl 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 168.0h， 以88%的产率得到(2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[3-(4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Synthesis of Glucosides Related to Grape and Wine Aroma Precursors

  摘要：

  Syntheses of the following glucosides are reported: 3',5',5'-trimethyl-3'-cyclohexenyl beta-D-glucopyranoside, 3'-(1 ''-cyclohexenyl)-1'-methyl-2'-propynyl-beta-D-glucopyranoside, (3'R*,9'S*)-3'-hydroxy-5'-megastigmen-7'-yn-9'-yl beta-D-glucopyranoside, (E,3'R*)-7'-oxo-5',8'-megastigmadien-3'-yl beta-D-glucopyranoside, and 4'-oxo-5'-megastigmen-9'-yl beta-D-glucopyranoside.

  DOI：

  10.1021/jf00052a025

文献信息

• Isolation of a Glucosidic β-Damascenone Precursor from Rose Petals
  作者：Markus Straubinger、Holger Knapp、Noriaki Oka、Naoharu Watanabe、Peter Winterhalter

  DOI：10.1021/jf970278j

  日期：1997.10.1

  The 9-O-beta-D-glucopyranoside of 3-hydroxy-7,8-didehydro-beta-ionol (1) has been isolated from a glycosidic XAD-2 extract obtained from rose petals. In addition to the beta-damascenone-generating compound 1, the following glycoconjugates have been isolated and characterized as peracetates: 3-hydroxy-7,8-dihydro-beta-ionol 9-O-beta-D-glucopyranoside (2), 3-hydroxy-7,8-dihydro-beta-ionol 3-O-beta-D-glucopyranoside (3), 2-phenylethyl-O-beta-D-glucopyranoside (4), 2-phenylethyl-O-beta-D-galactopyranoside (5), benzyl-O-beta-D-glucopyranoside (6), (2E)-2,6-dimethyl-6-hydroxyocta-2,7-dienyl-O-beta-D-glucopyranoside (7), (2Z)-2,6-dimethyl-6-hydroxyocta-2, 7-dienyl-O-beta-D-glucopyranoside (8), and (2E,6E)-2,6-dimethyl-1-hydroxyocta-2,6-dien-8-yl-O-beta-D-glucopyranoside (9).
• Synthesis of Glucosides Related to Grape and Wine Aroma Precursors
  作者：George K. Skouroumounis、Ralph A. Massy-Westropp、Mark A. Sefton、Patrick J. Williams

  DOI：10.1021/jf00052a025

  日期：1995.4

  Syntheses of the following glucosides are reported: 3',5',5'-trimethyl-3'-cyclohexenyl beta-D-glucopyranoside, 3'-(1 ''-cyclohexenyl)-1'-methyl-2'-propynyl-beta-D-glucopyranoside, (3'R*,9'S*)-3'-hydroxy-5'-megastigmen-7'-yn-9'-yl beta-D-glucopyranoside, (E,3'R*)-7'-oxo-5',8'-megastigmadien-3'-yl beta-D-glucopyranoside, and 4'-oxo-5'-megastigmen-9'-yl beta-D-glucopyranoside.