(2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(1-vinyl-allyloxy)-tetrahydro-pyran | 245369-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(1-vinyl-allyloxy)-tetrahydro-pyran
• 英文别名: (2R,3R,4S,5S,6S)-5-penta-1,4-dien-3-yloxy-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enyloxane
• CAS: 245369-14-6
• 化学式: C₃₅H₄₀O₅
• 分子量: 540.7
• InChiKey: SIOWPBWTECWWMN-PEINCPOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(1-vinyl-allyloxy)-tetrahydro-pyran 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 33.5h， 生成 [(E,2S)-4-[(2R,3R,4S,4aS,6S,9aS)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepin-6-yl]-2-acetyloxybut-3-enyl] acetate
  参考文献：
  名称：

  Expeditious tandem-metathesis route to the AB-ring fragment of ciguatoxin

  摘要：

  The AB-ring fragment of ciguatoxin was synthesized in ten steps from tri-O-benzyl-D-glucal based on a highly diastereoselective ring-closing metathesis and subsequent cross metathesis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01017-5
• 作为产物：
  描述：

  3-[(2S,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-enyloxan-3-yl]oxypent-4-ene-1,2-diol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以68%的产率得到(2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(1-vinyl-allyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  Expeditious tandem-metathesis route to the AB-ring fragment of ciguatoxin

  摘要：

  The AB-ring fragment of ciguatoxin was synthesized in ten steps from tri-O-benzyl-D-glucal based on a highly diastereoselective ring-closing metathesis and subsequent cross metathesis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01017-5

文献信息

• Expeditious tandem-metathesis route to the AB-ring fragment of ciguatoxin
  作者：Hiroki Oguri、Shin-ya Sasaki、Tohru Oishi、Masahiro Hirama

  DOI：10.1016/s0040-4039(99)01017-5

  日期：1999.7

  The AB-ring fragment of ciguatoxin was synthesized in ten steps from tri-O-benzyl-D-glucal based on a highly diastereoselective ring-closing metathesis and subsequent cross metathesis. (C) 1999 Elsevier Science Ltd. All rights reserved.