trans-5,6-dihydro-6-(hydroxymethyl)-2-methoxy-2H-pyran | 63358-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: trans-5,6-dihydro-6-(hydroxymethyl)-2-methoxy-2H-pyran
• 英文别名: [(2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]methanol
• CAS: 63358-55-4
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: USWZSVOYTUOFIM-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-5,6-dihydro-6-(hydroxymethyl)-2-methoxy-2H-pyran 在 六甲基磷酰三胺 、 ammonium heptamolybdate 、 双氧水 、 sodium hexamethyldisilazane 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 17.5h， 生成 triethyl-[(2S,3Z,5E)-4-ethyl-6-[(2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-2-methylhexa-3,5-dienoxy]silane
  参考文献：
  名称：

  Total Synthesis of (−)-Callystatin A

  摘要：

  [GRAPHICS]An effective total synthesis of (-)-callystatin A (1), member of the leptomycin family of antibiotics, has been achieved. The synthesis features Evans extended aldol methodology to construct the northern polypropionate subunit and two separate Julia olefinations to assemble the conjugated dienes. The total synthesis proceeded in 2.3% overall yield with the longest linear sequence of 15 steps.

  DOI：

  10.1021/ol0158922
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到trans-5,6-dihydro-6-(hydroxymethyl)-2-methoxy-2H-pyran
  参考文献：
  名称：

  Total Synthesis of (−)-Callystatin A

  摘要：

  [GRAPHICS]An effective total synthesis of (-)-callystatin A (1), member of the leptomycin family of antibiotics, has been achieved. The synthesis features Evans extended aldol methodology to construct the northern polypropionate subunit and two separate Julia olefinations to assemble the conjugated dienes. The total synthesis proceeded in 2.3% overall yield with the longest linear sequence of 15 steps.

  DOI：

  10.1021/ol0158922

文献信息

• Asymmetric Catalysis of Diels-Alder Cycloadditions by an MS-Free Binaphthol-Titanium Complex: Dramatic Effect of MS, Linear vs Positive Nonlinear Relationship, and Synthetic Applications
  作者：Koichi Mikami、Yukihiro Motoyama、Masahiro Terada

  DOI：10.1021/ja00086a014

  日期：1994.4

  Asymmetric Diels-Alder (D.-A.) reaction of 5-hydroxynaphthoquinone (juglone) with butadienyl acetate catalyzed by the binaphthol-derived chiral titanium (BINOL-Ti) complex 1 proceeds in only 9% ee in the presence of molecular sieves (MS). Remarkably, however, this reaction proceeds in 76-96% ee with BINOL-Ti complex 1 freed from MS to provide the endo-adducts useful for the synthesis of anthracyclines and tetracyclines. The solid MS-free BINOL-Ti complex 1 is stable for months at -20 degrees C, Enhancements in endo selectivity and asymmetric induction are observed with the MS-free BINOL-Ti 1 also in the catalyzed D.-A. cycloaddition of methacrolein and glyoxylate with 1,3-dienol ethers and esters. The glyoxylate adducts can be converted to the mevinolin (compactin) intermediates. Surprisingly, the MS-free complex 1 exhibits not only a linear relationship between the ee's of BINOL-Ti 1 and the D.-A. products but also a positive nonlinear effect (asymmetric amplification), depending simply on the mixing manner of (R)-1 with (S)-1 or (+/-)-1.
• JURCZAK, J.;BAUER, T.;FILIPEK, S.;TKACZ, M.;ZYGO, K., J. CHEM. SOC. CHEM. COMMUN., 1983, 9, 540-542
  作者：JURCZAK, J.、BAUER, T.、FILIPEK, S.、TKACZ, M.、ZYGO, K.

  DOI：——

  日期：——
• KONOWAL A.; BELNIAK K.; JURCZAK J.; CHMIELEWSKI O.; ACHMATOWICZ O. JR.; Z+, ROCZ. CHEM. <ROCH-AC>, 1976, 50, NO 3, 505-514
  作者：KONOWAL A.、 BELNIAK K.、 JURCZAK J.、 CHMIELEWSKI O.、 ACHMATOWICZ O. JR.、 Z+

  DOI：——

  日期：——
• Total Synthesis of (−)-Callystatin A
  作者：Amos B. Smith、Benjamin M. Brandt

  DOI：10.1021/ol0158922

  日期：2001.5.1

  [GRAPHICS]An effective total synthesis of (-)-callystatin A (1), member of the leptomycin family of antibiotics, has been achieved. The synthesis features Evans extended aldol methodology to construct the northern polypropionate subunit and two separate Julia olefinations to assemble the conjugated dienes. The total synthesis proceeded in 2.3% overall yield with the longest linear sequence of 15 steps.