methyl 3-O-α-D-glucopyranosyl-α-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-α-D-glucopyranosyl-α-D-mannopyranoside
• 英文别名: methyl α-D-glucopyranosyl-(1->3)-α-D-mannopyranoside；methyl (α-D-glucopyranosyl)-(1-3)-α-D-mannopyranoside；Glc(a1-3)a-Man1Me；(2R,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: WOKXHOIRHHAHDA-ATFWKMMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 在 10% palladium on active carbon 2,4,6-三甲基吡啶 、 ammonium cerium(IV) nitrate 、 氢气 、 silver trifluoromethanesulfonate 、 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 62.0h， 生成 methyl 3-O-α-D-glucopyranosyl-α-D-mannopyranoside
  参考文献：
  名称：

  A Synthetic Approach to the Glycan Chain of High Mannose Type N-Glycoprotein

  摘要：

  The syntheses of alpha-D-glucopyranose-(1-->3)-D-mannopyranose, methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranoside and methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranose-( 1--> 2)-alpha-D-mannopyranoside are reported. High stereoselectivity was observed during the coupling of glucose and mannose residues by the use of glucosyl trichloroacetimidate as donor.

  DOI：

  10.1080/07328309808001894

文献信息

• Synthesis and 13C NMR spectra of 2,3-di-O-glycosyl derivatives of methyl α-l-rhamnopyranoside and methyl α-d-mannopyranoside
  作者：Nikolay E. Nifant'ev、Alexander S. Shashkov、Grigory M. Lipkind、Nikolay K. Kochetkov

  DOI：10.1016/s0008-6215(92)84236-l

  日期：1992.12

  Abstract The syntheses are described of 2,3-di-O-glycosyl derivatives of methyl α- l - rhamnopyranoside (1–5)and α- d -mannopyranoside (6–9). Download : Download full-size image X Y X Y 1 α- l -Rha p α- d -Glc p 6 α- l -Rha p α- d -Glc p 2 α- d -Glc p α- l -Rha p 7 α- d -Man p α- d -Glc p 3 α- l -Rha p β- d -Glc p 8 β- l -Fuc p β- l -Fuc p 4 α- l -Rha p β- l -Fuc p 9 α- l -Fuc p β- l -Fuc p 5 β- d

  摘要描述了甲基α-1-鼠李糖吡喃糖苷（1-5）和α-d-甘露吡喃糖苷（6-9）的2，3-二-O-糖基衍生物的合成。下载：下载全尺寸图片XYXY 1α-l -Rha pα-d -Glc p 6α-l-Rha pα-d -Glc p 2α-d -Glc pα-l -Rha p 7α- d -Man pα-d -Glc p 3α-l-Rha pβ-d -Glc p 8β-l-Fuc pβ-1-Fuc p 4α-l-Rha pβ-1-Fuc p 9 α-1-Fuc pβ-1-Fuc p 5β-d-Glc pβ-d-Gal p与立体化学相关的三糖在13C NMR光谱中计算的加性偏差相似。
• Alternansucrase acceptor reactions with methyl hexopyranosides
  作者：Gregory L. Côté、Christopher A. Dunlap

  DOI：10.1016/s0008-6215(03)00324-0

  日期：2003.9

  pyranoside and methyl alpha-D-glucopyranosyl-(1-->4)-alpha-D-galactopyranoside, in a 2.5:1 molar ratio. Methyl D-allopyranosides were glucosylated primarily at position 6, yielding methyl alpha-D-glucopyranosyl-(1-->6)-D-allopyranosides. The latter subsequently gave rise to methyl alpha-D-glucopyranosyl-(1-->6)-alpha-D-glucopyranosyl-(1-->6)-D-allopyranosides. In general, the methyl alpha-D-hexopyranosides

  交替糖（EC 2.4.1.140，蔗糖：（1-> 6），（1-> 3）-α-D-葡聚糖6（3）-α-D-葡糖基转移酶）是一种D-葡聚糖酶，可合成来自蔗糖的与α-（1-> 3），（1-> 6）连接的D-葡聚糖。它还通过D-吡喃葡萄糖基转移到各种受体糖上来合成寡糖。我们已经研究了甲基糖苷作为模型化合物产生的受体产物，以便更好地了解交替糖蔗糖受体反应的特异性。由甲基β-D-吡喃葡糖苷产生的初始产物是甲基β-异麦芽糖苷，随后对其进行糖基化以生成甲基β-异麦芽三糖苷和甲基α-D-吡喃葡糖基-（1→3）-α-D-吡喃葡糖基-（ 1-> 6）-β-D-吡喃葡萄糖苷。这些产物类似于先前从甲基α-D-吡喃葡萄糖苷描述的那些。来自甲基α-D-甘露吡喃糖苷的主要初始受体产物是甲基α-D-吡喃葡萄糖基-（1→6）-α-D-甘露吡喃糖苷，但也分离并表征了一些次要产物，包括3,6-二-O-取代的甘露吡喃糖苷。甲基α-
• A Synthetic Approach to the Glycan Chain of High Mannose Type N-Glycoprotein
  作者：Slim Cherif、Jean-Marc Clavel、Claude Monneret

  DOI：10.1080/07328309808001894

  日期：1998.11

  The syntheses of alpha-D-glucopyranose-(1-->3)-D-mannopyranose, methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranoside and methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranose-( 1--> 2)-alpha-D-mannopyranoside are reported. High stereoselectivity was observed during the coupling of glucose and mannose residues by the use of glucosyl trichloroacetimidate as donor.