3,4-Anhydro-2-deoxy-D-threo-pentose diethyl acetal | 138665-68-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 3,4-Anhydro-2-deoxy-D-threo-pentose diethyl acetal
• 英文别名: 1,1-diethoxy-3R,4R-epoxypentane-5-ol；[(2R,3R)-3-(2,2-diethoxyethyl)oxiran-2-yl]methanol
• CAS: 138665-68-6
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: CJKKQLDFHOEESH-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-Anhydro-2-deoxy-D-threo-pentose diethyl acetal 在 2,6-二甲基吡啶 、 乙酸酐 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.33h， 生成
  参考文献：
  名称：

  Asymmetric synthesis of D- and L-2-deoxy-4-thioriboscs

  摘要：

  Both D- and L-enantiomers of 2-deoxy-4-thioribose derivatives 12 and 17 were prepared stereospecifically in 12 steps from 1,3-propanediol. The key intermediary 2,3-epoxy alcohols, 8 and 15 were obtained with high enantiomeric excess by the Sharpless asymmetric epoxidation using (+)-L-diethyl tartrate and (-)-D-diethyl tartrate.

  DOI：

  10.1016/s0957-4166(00)80489-9
• 作为产物：
  描述：

  3,3-二乙氧基-1-丙醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 草酰氯 、 D-(-)-酒石酸二乙酯 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 11.84h， 生成 3,4-Anhydro-2-deoxy-D-threo-pentose diethyl acetal
  参考文献：
  名称：

  Asymmetric synthesis of D- and L-2-deoxy-4-thioriboscs

  摘要：

  Both D- and L-enantiomers of 2-deoxy-4-thioribose derivatives 12 and 17 were prepared stereospecifically in 12 steps from 1,3-propanediol. The key intermediary 2,3-epoxy alcohols, 8 and 15 were obtained with high enantiomeric excess by the Sharpless asymmetric epoxidation using (+)-L-diethyl tartrate and (-)-D-diethyl tartrate.

  DOI：

  10.1016/s0957-4166(00)80489-9

文献信息

• A novel reagent for regioselective cleavage of 2,3-epoxyalcohols by fluoride - a synthesis of 3-fluoro-293-dideoxy-d-erythro-pentose.
  作者：Antonia A. Nikitenko、Boris M. Arshava、Igor E. Mikerin、Yuri E. Raifeld、Ving J. Lee、Stanley A. Lang

  DOI：10.1016/s0040-4039(00)60842-0

  日期：1992.11

  The cleavage of the oxirane ring of 3,4-anhydro-2deoxy-D-threo-pentose diethyl acetal by (isopropoxy)-titanium fluorides is discussed. The high regioselectivity found with bis(isopropoxy)titanium difluoride is the basis for an enantioselective synthesis of 3-fluoro-2,3-deoxy-D-erythreo-pentose from a non-carbohydrate precursor.

  讨论了由（异丙氧基）-钛氟化物裂解3,4-脱水-2-脱氧-D-苏-戊糖二乙缩醛的环氧乙烷环。用双（异丙氧基）二氟化钛发现的高区域选择性是从非碳水化合物前体对映选择性合成3-氟-2,3-脱氧-D-赤藓基-戊糖的基础。
• Acyloxy tri(isopropoxy)titanium reagents for regioselective cleavage of 2,3-epoxyalcohols. A synthesis of 2-deoxy-d-ribose.
  作者：Yuri E. Raifeld、Antonio Nikitenko、Boris M. Arshava

  DOI：10.1016/s0040-4020(01)86329-8

  日期：1993.3

  diethyl acetal by various acetic acid derivatives – titanium(IV) isopropoxide combinations are reported in detail. The high regioselectivity found with tri(isopropoxy)titanium acetate serves as the basis for a synthesis of 2-deoxy-D-ribose and its ethyl furanosides in high yields and optical purity from non-carbohydrate precursors. The synthesis of other acyloxy tri(isopropoxy)titanium reagents is also

  详细报道了各种乙酸衍生物-异丙醇钛（IV）组合对3,4-脱水-2-脱氧-D-苏-戊糖二乙缩醛的环氧乙烷环的裂解。用乙酸三（异丙氧基）钛发现的高区域选择性是从非碳水化合物前体以高收率和光学纯度合成2-脱氧-D-核糖及其乙基呋喃糖苷的基础。还描述了其他酰氧基三（异丙氧基）钛试剂的合成。
• Compounds of (i-PrO)3 TiX as novel reagents for regioselective oxirane ring opening
  作者：Yuri E. Raifeld、Anotonina A. Nikitenko、Boris M. Arshava

  DOI：10.1016/s0957-4166(00)82001-7

  日期：1991.1

  Substituted titanium (IV) triisopropoxides [(i-PrO)3TiX] are highly effective
• Asymmetric synthesis of D- and L-2-deoxy-4-thioriboscs
  作者：Jun'ichi Uenishi、Mitsuhiro Motoyamaand、Keiji Takahashi

  DOI：10.1016/s0957-4166(00)80489-9

  日期：1994.1

  Both D- and L-enantiomers of 2-deoxy-4-thioribose derivatives 12 and 17 were prepared stereospecifically in 12 steps from 1,3-propanediol. The key intermediary 2,3-epoxy alcohols, 8 and 15 were obtained with high enantiomeric excess by the Sharpless asymmetric epoxidation using (+)-L-diethyl tartrate and (-)-D-diethyl tartrate.