(2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-5-(3,4,5-trimethoxy-benzyloxy)-tetrahydro-pyran | 286425-50-1

• 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,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-5-(3,4,5-trimethoxy-benzyloxy)-tetrahydro-pyran
• 英文别名: (2R,3R,4S,5R,6R)-2-pent-4-enoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3-[(3,4,5-trimethoxyphenyl)methoxy]oxane
• CAS: 286425-50-1
• 化学式: C₄₂H₅₀O₉
• 分子量: 698.854
• InChiKey: MONNITSFIDAVLT-FLMPIELBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  51
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-5-(3,4,5-trimethoxy-benzyloxy)-tetrahydro-pyran 在 palladium on activated charcoal 吡啶 、 甲醇 、 ruthenium trichloride 、 sodium periodate 、 iodonium di(2,4,6-trimethylpyridine) perchlorate 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 21.0h， 生成 (2R,3S,4S,4aR,10bR)-3,4-Dihydroxy-2-hydroxymethyl-8,9,10-trimethoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
  参考文献：
  名称：

  Synthesis of bergenin-related natural products by way of an intramolecular C-glycosylation reaction

  摘要：

  The peracetate of tri-O-methylnorbergenin 16 as well as the cis-fused epimer of 16, which constitutes the core C-aryl glycosidic fragment of castacrenin B, were prepared by way of the IDCP-mediated intramolecular C-arylation of a pentenyl beta-D-glucopyranoside carrying, at O-2, a 3,4,5-trimethoxybenzyl substituent. (C) 2000 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00484-x
• 作为产物：
  描述：

  (3aR,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-methyl-2-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-b]pyran 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-5-(3,4,5-trimethoxy-benzyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  Synthesis of bergenin-related natural products by way of an intramolecular C-glycosylation reaction

  摘要：

  The peracetate of tri-O-methylnorbergenin 16 as well as the cis-fused epimer of 16, which constitutes the core C-aryl glycosidic fragment of castacrenin B, were prepared by way of the IDCP-mediated intramolecular C-arylation of a pentenyl beta-D-glucopyranoside carrying, at O-2, a 3,4,5-trimethoxybenzyl substituent. (C) 2000 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00484-x

文献信息

• Synthesis of bergenin-related natural products by way of an intramolecular C-glycosylation reaction
  作者：Cyril Rousseau、Olivier R Martin

  DOI：10.1016/s0957-4166(99)00484-x

  日期：2000.2

  The peracetate of tri-O-methylnorbergenin 16 as well as the cis-fused epimer of 16, which constitutes the core C-aryl glycosidic fragment of castacrenin B, were prepared by way of the IDCP-mediated intramolecular C-arylation of a pentenyl beta-D-glucopyranoside carrying, at O-2, a 3,4,5-trimethoxybenzyl substituent. (C) 2000 Elsevier Science Ltd, All rights reserved.