methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-altropyranoside | 74410-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-altropyranoside
• 英文别名: methyl 4,6-O-benzylidene-2-O-methyl-α-D-altropyranoside；2-OCH3-4,6-O-benzylidene-α-methyl-D-altroside；methyl-[O⁴,O⁶-((R)-benzylidene)-O²-methyl-α-D-altropyranoside]；Methyl-[O⁴,O⁶-((R)-benzyliden)-O²-methyl-α-D-altropyranosid]
• CAS: 74410-55-2
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: CMABQYQMHIOHML-LACSLYJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-altropyranoside 生成 methyl-[O3-benzoyl-O4,O6-((R)-benzylidene)-O2-methyl-α-D-altropyranoside]
  参考文献：
  名称：

  283.通过简单的光学反演将葡萄糖的衍生物转化为altrose的衍生物

  摘要：

  DOI：

  10.1039/jr9350001193
• 作为产物：
  描述：

  methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 甲醇 、 sodium methylate 作用下， 生成 methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-altropyranoside
  参考文献：
  名称：

  283.通过简单的光学反演将葡萄糖的衍生物转化为altrose的衍生物

  摘要：

  DOI：

  10.1039/jr9350001193

文献信息

• New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars
  作者：José M. Vega-Pérez、Ignacio Periñán、Margarita Vega-Holm、Carlos Palo-Nieto、Fernando Iglesias-Guerra

  DOI：10.1016/j.tet.2011.07.014

  日期：2011.9

  New D-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene). (C) 2011 Elsevier Ltd. All rights reserved.
• The use of pyridinium chlorochromate for preparation of hexopyranosiduloses without epimerisation
  作者：Brian B. Bissember、Richard H. Wightman

  DOI：10.1016/s0008-6215(00)85688-8

  日期：1980.5
• Regioselective Control in the Oxidative Cleavage of 4,6-<i>O</i>-Benzylidene Acetals of Glycopyranosides by Dimethyldioxirane
  作者：Arnaud Stévenin、François-Didier Boyer、Jean-Marie Beau

  DOI：10.1021/jo9026098

  日期：2010.3.5

  The oxidative cleavage of 4,6-O-benzylidene acetals of glycopyranosides using dimethyldioxirane (DMDO) leads to the corresponding hydroxy-benzoates lent yields. With a Proper choice of the neighboring protecting groups, this oxidative fragmentation provides the 6- or 4-hydroxyl derivatives in a highly regioselective manner.
• 2-METHYL-d-ALTROMETHYLOSE AND ITS BEARING ON THE CONFIGURATION OF DIGITALOSE
  作者：FRANK G. YOUNG、ROBERT C. ELDERFIELD

  DOI：10.1021/jo01197a005

  日期：1942.5
• Enantiospecific synthesis of 8-O-methylthioswainsonine from a derivative of D-glucose
  作者：Isidoro Izquierdo、Maria T Plaza、F Aragón

  DOI：10.1016/0957-4166(96)00330-8

  日期：1996.9

  The thioanalogue 1, (1R,2S,4S,8R,8 alpha S)-1,2,8-trihydroxy-8-O-methylthioindolizidine of 8-O-methylswainsonine 2 has been enantiospecifically synthesized from the important key intermediate methyl 2-O-methyl-3,6-thioanhydro-alpha-D-mannopyranoside 7, in five steps. Formation of the bicyclic system in 1 took place with a high stereoselectivity. Compound 7 was obtained in eight steps from the readily available methyl alpha-D-glucopyranoside. Copyright (C) 1996 Elsevier Science Ltd