[(2R)-1-(6-formyl-2,3-dihydro-1,4-dithiin-5-yl)-3-phenylmethoxypropan-2-yl] acetate | 294660-37-0

• 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: [(2R)-1-(6-formyl-2,3-dihydro-1,4-dithiin-5-yl)-3-phenylmethoxypropan-2-yl] acetate
• CAS: 294660-37-0
• 化学式: C₁₇H₂₀O₄S₂
• 分子量: 352.475
• InChiKey: LVAAOQTXKMYBIZ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R)-1-(6-formyl-2,3-dihydro-1,4-dithiin-5-yl)-3-phenylmethoxypropan-2-yl] acetate 在 三氟甲磺酸三甲基硅酯 、 TEA 、 镍 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 122.08h， 生成 (1R,2R,4R,6R)-2-methoxy-4-(phenylmethoxymethyl)-3,7-dioxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks

  摘要：

  4-Deoxy-L-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-L-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their D-series enantiomers.

  DOI：

  10.1021/jo0493774
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 吡啶 、 titanium(IV) isopropylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 [(2R)-1-(6-formyl-2,3-dihydro-1,4-dithiin-5-yl)-3-phenylmethoxypropan-2-yl] acetate
  参考文献：
  名称：

  Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks

  摘要：

  4-Deoxy-L-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-L-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their D-series enantiomers.

  DOI：

  10.1021/jo0493774

文献信息

• A New Approach to The Synthesis of Enantiomerically Pure 4-Deoxy Sugars
  作者：Romualdo Caputo、Annalisa Guaragna、Giovanni Palumbo、Silvana Pedatella、Francesco Solla

  DOI：10.1080/07328300008544104

  日期：2000.1

  alcohol anion equivalent and leads to three-carbon elongations of various electrophiles by introduction of a fully protected hydroxypropenyl moiety. The latter contains a double bond, which can be unravelled to the cis configuration by diastereoselective removal3 of the dimethylene-disulfur bridge, as well as a protected primary hydroxyl group that, depending on the deprotection conditions used (DDQ/NaBH4

  在最近的论文2中，我们报道了3 C锂化的5,6-二氢-1,4-二硫代-2-基[（4-甲氧基苄基）氧基]甲烷（1）的设计和合成。烯丙基醇阴离子当量，并通过引入受完全保护的羟基丙烯基部分，导致各种亲电试剂的三碳延伸。后者包含一个双键，该双键可通过非对映选择性去除二亚甲基-二硫桥的3分解为顺式构型，以及一个受保护的伯羟基，具体取决于所用的脱保护条件（DDQ / NaBH 4或DDQ） ，可能导致游离的烯丙醇或α，β-不饱和醛。
• A New Three Carbon Homologation<i>Via</i>Sulfur Containing Heterocyclic Systems
  作者：Romualdo Caputo、Annalisa Guaragna、Giovanni Palumbo、Silvana Pedatella

  DOI：10.1080/10426509908546495

  日期：1999.1

  reagent, based on a 5,6-dihydro-1,4-dithiin heterocyclic system1, has been devised and conveniently used for 3 carbon elongations of various electrophiles. In fact, it acts as either a propenyl alcohol or an acrolein anion equivalent, introducing into the new molecule a moiety consisting of fully protected double bond and allylic oxygen.

  一种基于 5,6-dihydro-1,4-dithiin 杂环系统的新试剂已被设计并方便地用于各种亲电子试剂的 3 个碳延伸。事实上，它充当丙烯醇或丙烯醛阴离子等价物，将一个由完全保护的双键和烯丙基氧组成的部分引入新分子。
• A Versatile Synthesis of Enantiomerically Pure D- and L-Pyranosyl Nucleoside Analogues
  作者：Romualdo Caputo、Annalisa Guaragna、Giovanni Palumbo、Silvana Pedatella

  DOI：10.1080/15257779908041529

  日期：1999.4

  2-[[O-(p-Methoxybenzyl)-oxy]methyl]-5,6-dihydro-1,4-dithiin 1 is a versatile three carbon homologation reagent which has been conveniently used in the synthesis of enantiomerically pure modified nucleosides.