(E)-(R)-5-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6-dimethyl-tetrahydro-pyran-2-yl]-5-hydroxy-pent-2-enoic acid methyl ester | 213754-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(R)-5-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6-dimethyl-tetrahydro-pyran-2-yl]-5-hydroxy-pent-2-enoic acid methyl ester
• 英文别名: methyl (E,5R)-5-hydroxy-5-[(2R,3S,5R,6S)-3-hydroxy-2,6-dimethyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)oxan-2-yl]pent-2-enoate
• CAS: 213754-84-8
• 化学式: C₂₉H₃₈O₇
• 分子量: 498.617
• InChiKey: FIPFQAQWQAQBMJ-KWUCRQIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-(R)-5-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6-dimethyl-tetrahydro-pyran-2-yl]-5-hydroxy-pent-2-enoic acid methyl ester 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 9-borabicyclo[3.3.1]nonane dimer 、 草酰氯 、 sodium hexamethyldisilazane 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[(2R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-4-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-propan-1-ol
  参考文献：
  名称：

  Synthesis of the AB ring system of gambierol

  摘要：

  Synthesis of the AB ring system of gambierol (1) was achieved from 2-deoxy-D-ribose. The key steps were the stereoselective allylation of the aldehyde 6, corresponding to the B ring, and the intramolecular hetero-Michael reaction of 9. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01310-0
• 作为产物：
  描述：

  (2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-carbaldehyde 在 sodium periodate 、 四氧化锇 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (E)-(R)-5-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6-dimethyl-tetrahydro-pyran-2-yl]-5-hydroxy-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of the AB ring system of gambierol

  摘要：

  Synthesis of the AB ring system of gambierol (1) was achieved from 2-deoxy-D-ribose. The key steps were the stereoselective allylation of the aldehyde 6, corresponding to the B ring, and the intramolecular hetero-Michael reaction of 9. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01310-0

文献信息

• Synthesis of the AB ring system of gambierol
  作者：Isao Kadota、Choul-Hong Park、Manabu Ohtaka、Nao Oguro、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(98)01310-0

  日期：1998.8

  Synthesis of the AB ring system of gambierol (1) was achieved from 2-deoxy-D-ribose. The key steps were the stereoselective allylation of the aldehyde 6, corresponding to the B ring, and the intramolecular hetero-Michael reaction of 9. (C) 1998 Elsevier Science Ltd. All rights reserved.