(2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester | 860267-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester
• 英文别名: ethyl 2-[(2R,3S,6R)-6-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3-hydroxyoxan-2-yl]acetate
• CAS: 860267-64-7
• 化学式: C₂₅H₃₂O₆
• 分子量: 428.525
• InChiKey: BENRKTASUOZCDF-OLKYXYMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester 在 sodium hydroxide 、 正丁基锂 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 37.0h， 生成 (2R,3R,6R)-6-((R)-1,2-Bis-benzyloxy-ethyl)-3-methoxymethoxy-2-((Z)-tetradec-2-enyl)-tetrahydro-pyran
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure for Pyragonicin

  摘要：

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.

  DOI：

  10.1021/ol0508126
• 作为产物：
  描述：

  (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane 在 四氧化锇 N-甲基吗啉 、 甲醇 、 sodium periodate 、 samarium diiodide 、 D(+)-10-樟脑磺酸 、 四丁基碘化铵 、 zinc trifluoromethanesulfonate 、 sodium hydride 、 碳酸氢钠 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 71.5h， 生成 (2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure for Pyragonicin

  摘要：

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.

  DOI：

  10.1021/ol0508126

文献信息

• Total Synthesis of the Proposed Structure for Pyragonicin
  作者：Shunya Takahashi、Narihito Ogawa、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1021/ol0508126

  日期：2005.6.1

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.