methyl α-L-rhamnopyranosyl-(1->3)-β-L-rhamnopyranosyl-(1->4)-α-D-glucopyranoside | 1028832-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-L-rhamnopyranosyl-(1->3)-β-L-rhamnopyranosyl-(1->4)-α-D-glucopyranoside
• 英文别名: methyl -L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-α-D-glucopyranoside；Rha(a1-3)Rha(b1-4)a-Glc1Me；(2S,3R,4R,5R,6S)-2-[(2R,3R,4R,5S,6S)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 1028832-96-3
• 化学式: C₁₉H₃₄O₁₄
• 分子量: 486.471
• InChiKey: GWZXZHUYZKVDFQ-HTXFEOLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  217
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  methyl 2,4-di-O-benzyl-3-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2,4-di-O-benzyl-β-L-rhamnopyranosyl-(1→4)2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 sodium methylate 、 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以96%的产率得到methyl α-L-rhamnopyranosyl-(1->3)-β-L-rhamnopyranosyl-(1->4)-α-D-glucopyranoside
  参考文献：
  名称：

  C3-酯基对L-鼠李糖吡喃糖硫糖苷供体糖基化立体化学的立体定向作用：α-和β-L-鼠李糖吡喃糖苷的立体选择性合成

  摘要：

  描述了C3-酯基团对Lrhamnopyranose（L-Rha）乙基硫代糖苷的糖基化立体化学的调节作用。带有L-Rha硫糖苷的3-O-芳基羰基或乙酰丙酰基经历高度α-选择性糖基化作用，而3-O-4-亚硝基甲酰基和2-吡嗪羰基L-Rha硫糖苷的糖基化表现出β-立体选择性

  DOI：

  10.1002/ejoc.201901186

文献信息

• Stereoselective Synthesis of β-<scp>l</scp>-Rhamnopyranosides
  作者：Yong Joo Lee、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1021/ja801574q

  日期：2008.5.1

  Stereoselective construction of 1,2-cis-beta-L-rhamnopyranoside was achieved by our effective methodology using naphthylmethyl (NAP) ether-mediated intramolecular aglycon delivery (IAD). The complete stereoselective synthesis of the bacterial extracellular polysaccharide, alpha-L-Rhap-(1 -> 3)-beta-L-Rhap-(1 -> 4)Glcp from Sphaerotilus natans, was successfully accomplished, clearly demonstrating that the NAP-IAD methodology is highly versatile.
• Stereodirecting Effect of C3-Ester Groups on the Glycosylation Stereochemistry of L-Rhamnopyranose Thioglycoside Donors: Stereoselective Synthesis of α- and β-L-Rhamnopyranosides
  作者：Jin-Cai Lei、Yu-Xiong Ruan、Sheng Luo、Jin-Song Yang

  DOI：10.1002/ejoc.201901186

  日期：2019.10.9

  tuning effect of C3‐ester groups on the glycosylation stereochemistry of Lrhamnopyranose (L‐Rha) ethyl thioglycosides is described. The 3‐O‐arylcarbonyl or levulinoyl carrying L‐Rha thioglycosides undergo highly α‐selective glycosylation while the glycosylation of the 3‐O‐4‐nitropicoloyl and 2‐pyrazinecarbonyl L‐Rha thioglycosides displays β‐stereoselectivity

  描述了C3-酯基团对Lrhamnopyranose（L-Rha）乙基硫代糖苷的糖基化立体化学的调节作用。带有L-Rha硫糖苷的3-O-芳基羰基或乙酰丙酰基经历高度α-选择性糖基化作用，而3-O-4-亚硝基甲酰基和2-吡嗪羰基L-Rha硫糖苷的糖基化表现出β-立体选择性