3-deoxy-3-C-[(Z)-(methoxycarbonyl)methylene]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 18427-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-3-C-[(Z)-(methoxycarbonyl)methylene]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: (Z)-(O¹,O²;O⁵,O⁶-diisopropylidene-α-D-ribo-hexofuranos-3-ylidene)-acetic acid methyl ester；O¹,O²;O⁵,O⁶-diisopropylidene-3-(Z)-methoxycarbonylmethylene-α-D-ribo-3-deoxy-hexofuranose；methyl (2Z)-2-[(3aR,5S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-ylidene]acetate
• CAS: 18427-17-3
• 化学式: C₁₅H₂₂O₇
• 分子量: 314.335
• InChiKey: XXXBUSBFUCCECF-LWMFCTBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-deoxy-3-C-[(Z)-(methoxycarbonyl)methylene]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 咪唑 、 4-二甲氨基吡啶 、 Amberlite IR 120H 、 水 、 二异丁基氢化铝 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 30.92h， 生成 5,6-bis(O-tert-butyldimethylsilyl)-3-deoxy-1,2-O-isopropylidene-3-C-(Z)-(2-thiocyanatoethylidene)-α-D-glucofuranose
  参考文献：
  名称：

  Creation of quarternary stereocentres via [3,3]-sigmatropic rearrangement of allylic thiocyanates. A synthetic approach to (+)-myriocin

  摘要：

  A stereoselective approach to the advanced precursor of (+)-myriocin, 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-alpha-D-glucofuranose 3-C-carboxylic acid, via the [3,3]-sigmatropic rearrangement of allylic thiocyanates prepared from D-glucose is presented. From the observed results, supported by DFT calculations, we can conclude that the [3,3]-sigmatropic rearrangement of the thiocyanato group in allylic hexofuranosides is strongly influenced by the steric interaction of the 1,2-O-isopropylidene group in the transition states. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.032

文献信息

• Electrophilic additions to 3-C-[(methoxycarbonyl)methyl]-3-deoxy-D-ribofuranose enolates: a case of unusually efficient nonchelate-enforced chirality transfer
  作者：Johann. Mulzer、Ulrich. Steffen、Ludwig. Zorn、Christian. Schneider、Elmar. Weinhold、Winfried. Muench、Rainer. Rudert、Peter. Luger、Hans. Hartl

  DOI：10.1021/ja00222a024

  日期：1988.7

  Les halogenures d'alkyles et le benzaldehyde s'additionnent a l'enolate de lithium du compose du titre avec une diastereoselectivite superieure a 99%

  卤代烷烃和苯甲醛添加剂 a l'enolate delithium du compose du titre avec une diastereoselectivite superieure a 99%
• Synthesis of glycos-3-yl-α,γ-diamino acids. Synthesis of four diastereomeric spiro-3,4′-(R and S)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-d-ribo-hexofuranose)-3′-(R and S)-acetamido-2′-pyrrolidinones
  作者：Alex Rosenthal、Kent Dooley

  DOI：10.1016/s0008-6215(00)85948-0

  日期：1976.12

  analysis of compounds 8 and 10 showed them to be spiro-3,4′-( R )-(3-deoxy-1,2:5,6-di- O -isopropylidine-α- d - ribo -hexofuranose)-3′-( R )-[and 3′-( S )]-acetamido-2′-pyrrolidinone, respectively. The structures of compounds 4 and 6 (determined by chemical means) were the corresponding spiro-3,4′-( S )-3′-( R )-acetamido-2′-pyrrolidinone and 3′-( S )-acetamido-2′-pyrrolidinone, respectively.

  摘要用重氮甲烷在乙醚中处理（Z）-3-脱氧-1,2：5,6-二-O-异丙基-3-C-（甲氧羰基）-亚甲基-α-d-核糖-六呋喃糖（1）不稳定的Δ1-和Δ2-吡唑啉2和2a。后一种化合物在阮内镍上的高压氢化得到胺3、5、7和9的混合物（产率为80％），将其通过色谱分离。这些化合物的乙酰化产生N-乙酰基衍生物4、6、8和10。化合物8和10的X射线分析表明它们为螺-3,4'-（R）-（3-脱氧-1,2：5,6-二-O-异丙基-α-d-核糖-六呋喃糖）-3'-（R）-[和3'-（S）]-乙酰氨基-2'-吡咯烷酮。化合物4和6的结构（通过化学方法确定）为相应的spiro-3,4'-（S）-3'-（R）-乙酰氨基-2'-吡咯烷酮和3'-（S）-乙酰氨基- 2'-吡咯烷酮
• Cu(OTf)2-promoted efficient synthetic route towards glycospiro-pyrrolo[2,1-a]isoquinolines
  作者：Piyali Deb Barman、Ishita Sanyal、Sukhendu B. Mandal、Asish Kumar Banerjee

  DOI：10.1016/j.tetlet.2014.08.076

  日期：2014.10

  A simple, convenient and efficient protocol for the construction of an array of glycospiro-pyrroloisoquinolines using isoquinolinium ylide and a carbohydrate-derived exocyclic olefin in the presence of Cu(OTf)(2)-Et3N catalytic system is described. Isoquinoline and alkylbromoacetates/2-bromoacetophenones were employed to generate the azomethine ylides in the presence of Et3N in refluxing toluene and subsequent exposure to the olefin led to the desired isoquinoline derivatives. (C) 2014 Elsevier Ltd. All rights reserved.
• MULZER, JOHANN;STEFFEN, ULRICH;ZORN, LUDWIG;SCHNEIDER, CHRISTIAN;WEINHOLD+, J. AMER. CHEM. SOC., 110,(1988) N 14, 4640-4646
  作者：MULZER, JOHANN、STEFFEN, ULRICH、ZORN, LUDWIG、SCHNEIDER, CHRISTIAN、WEINHOLD+

  DOI：——

  日期：——