allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-β-D-glucopyranoside | 866325-73-7

• 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: allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-β-D-glucopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)]Xyl(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Glc(b)-O-allyl；[(3R,4S,5R,6R)-4,5-dibenzoyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-prop-2-enoxyoxan-2-yl]methoxy]oxan-3-yl] benzoate
• CAS: 866325-73-7
• 化学式: C₅₆H₄₈O₁₆
• 分子量: 976.988
• InChiKey: OHRAYLKRCVJBHK-RVPGYJCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  72
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  195
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-β-D-glucopyranoside 在 lithium acetate 、 sodium methylate 、 copper diacetate 、 palladium diacetate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 cinnamyl 6'-O-(β-D-xylopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Rosavin and its analogues based on a Mizoroki-Heck type reaction

  摘要：

  The Rosavin framework could be constructed with either phenylboronic acids, the protected arabinopyranosyl bromide 4 or the protected xylopyranosyl bromide 5, along with allyl O-beta-D-glucopyranoside 7 that could be easily prepared based on direct beta-glucosidation between allyl alcohol and D-glucose using the immobilized beta-glucosidase (EC 3.2.1.21). The key reaction was the Pd(II)-catalyzed Mizoroki-Heck type reaction between allyl beta-D-glucopyranoside congeners 9 or 10 and arylboronic acids. Deprotection of the coupling products afforded synthetic Rosavin 1, 4-methoxycinnamyl 6-O-(alpha-L-arabinopyranosyl)-beta-D-glucopyranoside 2, and cinnamyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyrano side 3, which were identical with the natural products in respect to the specific rotation and spectral data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.040
• 作为产物：
  描述：

  allyl 6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 在 吡啶 、 盐酸 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Rosavin and its analogues based on a Mizoroki-Heck type reaction

  摘要：

  The Rosavin framework could be constructed with either phenylboronic acids, the protected arabinopyranosyl bromide 4 or the protected xylopyranosyl bromide 5, along with allyl O-beta-D-glucopyranoside 7 that could be easily prepared based on direct beta-glucosidation between allyl alcohol and D-glucose using the immobilized beta-glucosidase (EC 3.2.1.21). The key reaction was the Pd(II)-catalyzed Mizoroki-Heck type reaction between allyl beta-D-glucopyranoside congeners 9 or 10 and arylboronic acids. Deprotection of the coupling products afforded synthetic Rosavin 1, 4-methoxycinnamyl 6-O-(alpha-L-arabinopyranosyl)-beta-D-glucopyranoside 2, and cinnamyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyrano side 3, which were identical with the natural products in respect to the specific rotation and spectral data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.040

文献信息

• Synthesis of Rosavin and its analogues based on a Mizoroki-Heck type reaction
  作者：Msashi Kishida、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2005.06.040

  日期：2005.8

  The Rosavin framework could be constructed with either phenylboronic acids, the protected arabinopyranosyl bromide 4 or the protected xylopyranosyl bromide 5, along with allyl O-beta-D-glucopyranoside 7 that could be easily prepared based on direct beta-glucosidation between allyl alcohol and D-glucose using the immobilized beta-glucosidase (EC 3.2.1.21). The key reaction was the Pd(II)-catalyzed Mizoroki-Heck type reaction between allyl beta-D-glucopyranoside congeners 9 or 10 and arylboronic acids. Deprotection of the coupling products afforded synthetic Rosavin 1, 4-methoxycinnamyl 6-O-(alpha-L-arabinopyranosyl)-beta-D-glucopyranoside 2, and cinnamyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyrano side 3, which were identical with the natural products in respect to the specific rotation and spectral data. (c) 2005 Elsevier Ltd. All rights reserved.