(2S,6S)-6-hydroxymethyl-2-methoxy-5,6-dihydro-2H-pyran | 63358-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,6S)-6-hydroxymethyl-2-methoxy-5,6-dihydro-2H-pyran
• 英文别名: (2S)-methoxy-(6S)-hydroxymethyl-5,6-dihydro-2H-pyran；trans-6-Hydroxymethyl-2-methoxy-5,6-dihydro-2H-pyran；[(2S,6S)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]methanol
• CAS: 63358-54-3
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: USWZSVOYTUOFIM-BQBZGAKWSA-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：

  (2S,6S)-6-hydroxymethyl-2-methoxy-5,6-dihydro-2H-pyran 在 吡啶 、 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 49.0h， 生成 methyl 2,3-anhydro-4,6-dideoxy-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Syntheses of deoxyhexoses from diastereoisomerically pure hetero-Diels-Alder adduct

  摘要：

  Syntheses of deoxyhexoses are presented. The concept is based on the functionalization of enantiomerically pure 6-hydroxymethyl-2-methoxy-5,6-dihydro-2H-pyran, which is easily synthesized by asymmetric hetero-Diels-Alder reaction. Methyl 4,6-dideoxy-alpha-D-arabino-hexopyranoside, methyl alpha-D-chalcoside and methyl alpha-D-desosanimide are synthesized. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00159-2
• 作为产物：
  描述：

  methyl 2,3-dideoxy-4,6-dihydroxy-α-D-erythro-hex-2-enopyranoside 在 吡啶 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 (2S,6S)-6-hydroxymethyl-2-methoxy-5,6-dihydro-2H-pyran
  参考文献：
  名称：

  Total Synthesis of S-(+)-Argentilactone

  摘要：

  摘要：通过使用甲基-α-D-葡萄糖吡喃糖(3)作为碳水化合物模板，完成了S-(+)-argentilactone (2)的不对称全合成。苄亚甲基缩醛5经过t-BuOOH/AlCl3水解，并进一步处理得到醛10。Wittig反应和后续的缩醛位置氧化产生了目标argentilactone。

  DOI：

  10.1515/znb-2001-0318

文献信息

• Asymmetric catalysis of Diels–Alder cycloaddition by a β-amino alcohol derived boron complex: reasonable transition-state assembly for one-directional diene approach
  作者：Yukihiro Motoyama、Koichi Mikami

  DOI：10.1039/c39940001563

  日期：——

  Asymmetric Diels–Alder reactions of glyoxylate with acid-labile Danishefsky dienes are catalysed in high enantio- and cis(endo)-diastereo-selectivity by a chiral amino alcohol derived boron complex, via the favourable transition-state assembly for one-directional diene-approach from the site proximal to the sulfonylamino moiety.

  由手性氨基醇衍生的硼络合物催化甘油酸与酸敏感的Danishefsky二烯的非对称Diels-Alder反应，实现了高对映选择性和cis(endo)非对映选择性，这是通过从邻近磺酰氨基的位点进行单向二烯接近的有利过渡态组装实现的。
• Asymmetric induction in the high-pressure cycloaddition of 2,3-O-isopropylidene-D-glyceraldehyde to 1-methoxybuta-1,3-diene
  作者：Janusz Jurczak、Tomasz Bauer、Stanislaw Filipek、Marek Tkacz、Krystyna Zygo

  DOI：10.1039/c39830000540

  日期：——

  The high-pressure cycloaddition of 2,3-O-isopropylidene-D-glyceraldehyde (7) to 1-methoxybuta-1,3-diene (1) afforded the diastereoisomeric cycloadducts (3) for which the diastereoisomeric excess and absolute configuration have been determined.

  2,3-的高压环加成ö异亚丙基d甘油醛（7）至1-methoxybuta -1,3-二烯（1），得到非对映异构cycloadducts（3为其非对映异构过量和绝对构型已经）决心。
• Stereochemical course of the [4+2] cycloaddition of 1-methoxybuta-1,3-diene to N-glyoxyloyl-(2R)-bornane-10,2-sultam. The formal synthesis of compactin and mevinolin
  作者：Tomasz Bauer、Christian Chapuis、Artur Jez̀ewski、Janusz Kozak、Janusz Jurczak

  DOI：10.1016/0957-4166(96)00156-5

  日期：1996.5

  ne-10,2-sultam 2, readily prepared from (2R)-bornane-10,2-sultam 1, was used in noncatalyzed atmospheric and high-pressure as well as in [Eu(fod)3]-catalyzed [4+2] cycloadditions with 1-methoxybuta-1,3-diene 3. All the [4+2] cycloadditions studied led to diastereoisomeric mixtures of 6-substituted derivatives of 2-methoxy-5,6-dihydro-2H-pyran 4–7. The extent of asymmetric induction in these reactions

  手性heterodienophile Ñ -glyoxyloyl-（2 - [R）-bornane-10,2-磺内酰胺2，容易从（2制备- [R）-bornane-10,2-磺内酰胺1，在非催化常压和高压用以及在[Eu（fod）3 ]催化的1-4-甲氧基-1,3-二烯3的[4 + 2]环加成反应中。所有研究的[4 + 2]环加成反应均导致2-甲氧基-5,6-二氢-2H-吡喃4-7的6-取代衍生物的非对映异构体混合物。通过1 H NMR分析和热力学稳定产物5和7的绝对构型，确定了这些反应中的不对称诱导程度。通过X射线分析，并通过化学相关独立进行。提出了针对非催化和[Eu（fod）3 ]促进的反应的立体化学模型。然后将[4 + 2]环加合物5有效地转化为（4 R）-羟基-（6S）-羟甲基四氢吡喃酮2 12，这是Compactin 10和mevinolin 11内酯部分的关键合成子。
• Diastereoselective synthesis of the lactone portion of compactin and mevinolin
  作者：Tomasz Bauer、Janusz Kozak、Christian Chapuis、Janusz Jurczak

  DOI：10.1039/c39900001178

  日期：——

  The highly diastereoselective [4 + 2] cycloaddition of 1-methoxybuta-1,3-diene (3) to (2R)-N-glyoxyloylbornane-10,2-sultam (2) afforded the adduct (4) which was effectively transformed into (4R,6S)-4-hydroxy-6-hydroxymethyltetrahydro-2-pyrone (1), a key synthon for the lactone moiety of compactin and mevinolin.

  将1-甲氧基丁1,3-二烯（3）高度非对映选择性的[4 + 2]环加成（2 R）-N-乙氧基乙酰冰片烷10,2-磺酰胺（2）提供加合物（4），该加合物可以有效地转化进入（4 R，6 S）-4-羟基-6-羟甲基四氢-2-吡喃酮（1），这是紧缩蛋白和美维林的内酯部分的关键合成子。
• Chiral Phosphoric Acid-Governed Anti-Diastereoselective and Enantioselective Hetero-Diels−Alder Reaction of Glyoxylate
  作者：Norie Momiyama、Hideaki Tabuse、Masahiro Terada

  DOI：10.1021/ja904749x

  日期：2009.9.16

  A highly enantioselective anti-diastereoselective hetero-Diets-Alder reaction between a glyoxylate and siloxy- or methoxydienes using a chiral phosphoric acid catalyst that possesses less bulky phenyl groups at the 3 and 3' positions of binaphthyl has been developed. The diastereoselectivities presented are disparate to those previously reported for hetero-Diets-Alder reactions catalyzed by a chiral Lewis acid.