Methyl 2,4-di-O-benzyl-3-O-α-L-rhamnopyranosyl-α-L-rhamnopyranoside | 144174-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,4-di-O-benzyl-3-O-α-L-rhamnopyranosyl-α-L-rhamnopyranoside
• 英文别名: methyl 2,4-di-O-benzyl-3-O-α-L-rhanmopyranosyl-α-L-rhamnopyranoside
• CAS: 144174-62-9
• 化学式: C₂₇H₃₆O₉
• 分子量: 504.577
• InChiKey: KRKNGXBARHHUQZ-OPZKIZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  116.07
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Methyl 2,4-di-O-benzyl-3-O-α-L-rhamnopyranosyl-α-L-rhamnopyranoside 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (3aR,4S,6S,7S,7aR)-7-Allyloxy-4-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran
  参考文献：
  名称：

  Mukherjee, Atreyee; Roy, Nirmolendu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 8, p. 726 - 728

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 在 sodium hydroxide 、 4 A molecular sieve 、 四丁基溴化铵 、 sodium methylate 、 氰化汞 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 31.0h， 生成 Methyl 2,4-di-O-benzyl-3-O-α-L-rhamnopyranosyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Mukherjee, Atreyee; Roy, Nirmolendu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 8, p. 726 - 728

  摘要：

  DOI：

文献信息

• Synthesis and 13C-n.m.r. spectroscopic investigation of three methyl rhamnotriosides
  作者：András Lipták、János Harangi、Gyula Batta、Otto Seligmann、Hildebert Wagner

  DOI：10.1016/0008-6215(84)85401-4

  日期：1984.8

  Abstract Methyl 2,3-O-isopropylidene-4-O-(2,3-O-isopropylidene-α- l -rhamnopyranosyl)- α- l -rhamnopyranoside, methyl 2,4-di-O-benzyl-3-O-(2,3-O-isopropylidene- α- l -rhamnopyranosyl)-α- l -rhamnopyranoside, and methyl 3,4-di-O-benzyl-2-O- (2,3-O-isopropylidene-α- l -rhamnopyranosyl)-α- l -rhamnopyranoside, obtained by isopropylidenation of the respective methyl rhamnobiosides, were glycosylated with

  摘要2,3-O-异亚丙基-4-O-（2,3-O-异亚丙基-α-1-鼠李糖基吡喃糖基）-α-1-l-鼠李糖吡喃糖苷，甲基2,4-二-O-苄基-3-O -（2,3-O-异亚丙基-α-1-鼠李吡喃糖基）-α-1-鼠李吡喃糖苷和甲基3,4-二-O-苄基-2-O-（2,3-O-异亚丙基-α-通过各个甲基鼠李糖苷的异丙基化获得的1-鼠李糖吡喃糖基）-α-1-鼠李糖吡喃糖苷被2,3,4-三-O-乙酰基-α-1-鼠李糖吡喃糖基溴化物糖基化。从产物中除去保护基，得到α-1-Rhap-（1→4）-α-1-Rhap-（1→4）-α-1-Rhap，α-1-Rhap-（ 1→4）-α-l-Rhap-（1→3）-α-l-Rhap和α-1-Rhap-（1→4）-α-l-Rhap-（1→2）-α- l -Rhap。这些三糖苷及其七乙酸盐已通过13C-nmr光谱法进行了研究。
• Synthesis of methyl 3-O-(2-O-methyl-α-l-fucopyranosyl)-α-l-rhamnopyranoside, methyl 3-O-α-l-rhamnopyranosyl-α-d-glucopyranoside, and methyl 3-O-[3-O-(2-O-methyl-α-l-fucopyranosyl)-α-l-rhamnopyranosyl]-α-l-rhamnopyranoside: di- and tri-saccharide segments of a lipo-oligosaccharide (LOS-1) of Mycobacterium szulgai
  作者：Mukund K. Gurjar、Prathama S. Mainkar

  DOI：10.1016/0008-6215(93)84227-w

  日期：1993.2
• Synthesis of methyl 3--[3--(2,3,4-tri--methyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside : The outer trisaccharide unit of a unique glycopeptidolipid
  作者：Mukund K Gurjar、Anupama S Mainkar

  DOI：10.1016/s0040-4020(01)80018-1

  日期：1992.1

  The combination of sugars present in Mycobacterium xenopi glycopeptidolipid (GPL X-1) has been characterised as O-(2,3,4-tri-O-methyl-alpha-L-rhamnopyranosyl)-(1-3)-O-(alpha-L-rhamnopyranosyl)-(1-3)-O-(alpha-L-rhamnopyranosyl)-(1-3)-6-deoxy-L-glucose. Two synthetic routes (A and B) towards the outer trisaccharide segment (2) have been designed. Route A involved the condensation of the aglycone (7) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl bromide (13) to afford which was sequentially deacetylated, methylated, deallylated and reacetylated to afford 12. Condensation of 12 with 16 in the presence of borontrifluoride etherate was unsuccessful. In route B, the disaccharide 21 was synthesised by the coupling reaction between 16 and 18 in the presence of borontrifluoride-etherate followed by deallylation. Alternatively, the disaccharide triacetate (22) was first prepared and routine modifications on it led to the formation of 21. Final condensation of 21 with the trichloroacetimidate (29) followed by sequential deacetylation, methylation and debenzylation afforded the trisaccharide (2).