3-deoxy-1,2:5,6-di-O-isopropylidene-(3S)-3,3-C-[(S)-(hydroxymethyl)ethylene]-α-D-ribo-hexofuranose | 214400-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-1,2:5,6-di-O-isopropylidene-(3S)-3,3-C-[(S)-(hydroxymethyl)ethylene]-α-D-ribo-hexofuranose
• 英文别名: [(1'S,3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylspiro[5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-6,2'-cyclopropane]-1'-yl]methanol
• CAS: 214400-78-9
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: WQUMYTICUACEKX-FWGJMNDOSA-N

物化性质

• 沸点：
  390.5±42.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-deoxy-1,2:5,6-di-O-isopropylidene-(3S)-3,3-C-[(S)-(hydroxymethyl)ethylene]-α-D-ribo-hexofuranose 在 Grubbs catalyst first generation 偶氮二异丁腈 、 dimethyl sulfide borane 、 diethylzinc 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  通过带有（甲基）烯丙基三丁基锡的（卤甲基）环丙烷的开环获得的带有宝石-二烯丙基取代基的杂环的闭环易位合成螺环。

  摘要：

  在烯丙基三正丁基锡-AIBN的存在下，环丙基甲基溴化物/黄药发生开环反应，并同时以高收率形成双键二烯丙基衍生物。用Grubbs的催化剂在双烯丙基二烯丙基衍生物上进行的闭环易位反应提供了螺环戊烯基产物。这两种方法的结合已应用于合成单，双环戊基碳水化合物以及螺环戊基脯氨酸衍生物。

  DOI：

  10.1039/b300314k
• 作为产物：
  描述：

  二碘甲烷 、 (Z)-3-deoxy-3-C-[(hydroxymethyl)methylene]-1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose 在 diethylzinc 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到3-deoxy-1,2:5,6-di-O-isopropylidene-(3S)-3,3-C-[(S)-(hydroxymethyl)ethylene]-α-D-ribo-hexofuranose
  参考文献：
  名称：

  Synthesis and Application of 3,3-Spirocyclopropane Derivatives Obtained from 1,2:5,6-Di-O-Isopropylidene-α-D-Glucofuranose

  摘要：

  3,3-Spirocyclopropane derivatives (5 and 7) were prepared by three different methods of cyclopropanation starting from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (2). Subsequent radical induced cyclopropane ring opening reaction stereospecifically provided the 3-C-allyl derivative (9). However, activation of the cyclopropyl ring through the aldehyde (10) followed by hydrogenation gave a quaternary chiral derivative (11) which was elaborated to the versatile intermediate (1) by using Bamford-Stevens reaction.

  DOI：

  10.1080/07328309808001887

文献信息

• Synthesis of spirocycles via ring closing metathesis of heterocycles carrying gem-diallyl substituents obtained via ring opening of (halomethyl)cyclopropanes with allyltributyltin
  作者：Mukund K. Gurjar、Somu V. Ravindranadh、Kuppusamy Sankar、Sukhen Karmakar、Joseph Cherian、Mukund S. Chorghade

  DOI：10.1039/b300314k

  日期：2003.4.14

  In the presence of allyl tri-n-butyltin--AIBN, cyclopropylmethyl bromides/xanthates undergo ring-opening reaction with concomitant formation of geminal diallyl derivatives in good yields. The ring closing metathesis reactions on geminal diallyl derivatives with Grubbs' catalyst provided spirocyclopentenyl products. Combination of these two methodologies has been applied to the synthesis of mono-,

  在烯丙基三正丁基锡-AIBN的存在下，环丙基甲基溴化物/黄药发生开环反应，并同时以高收率形成双键二烯丙基衍生物。用Grubbs的催化剂在双烯丙基二烯丙基衍生物上进行的闭环易位反应提供了螺环戊烯基产物。这两种方法的结合已应用于合成单，双环戊基碳水化合物以及螺环戊基脯氨酸衍生物。
• Synthesis and Application of 3,3-Spirocyclopropane Derivatives Obtained from 1,2:5,6-Di-<i>O</i>-Isopropylidene-α-D-Glucofuranose
  作者：M. K. Gurjar、B. V. N. B. S. Sharma、B. Venkateswara Rao

  DOI：10.1080/07328309808001887

  日期：1998.9.1

  3,3-Spirocyclopropane derivatives (5 and 7) were prepared by three different methods of cyclopropanation starting from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (2). Subsequent radical induced cyclopropane ring opening reaction stereospecifically provided the 3-C-allyl derivative (9). However, activation of the cyclopropyl ring through the aldehyde (10) followed by hydrogenation gave a quaternary chiral derivative (11) which was elaborated to the versatile intermediate (1) by using Bamford-Stevens reaction.