methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside | 144174-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside
• 英文别名: Methyl 2,4-di-O-benzyl-3-O-(4-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside；Bn(-4)Rha(a1-3)[Bn(-2)][Bn(-4)]a-Rha1Me；(2S,3R,4S,5R,6S)-2-[(2R,3R,4R,5S,6S)-2-methoxy-6-methyl-3,5-bis(phenylmethoxy)oxan-4-yl]oxy-6-methyl-5-phenylmethoxyoxane-3,4-diol
• CAS: 144174-64-1
• 化学式: C₃₄H₄₂O₉
• 分子量: 594.702
• InChiKey: KKFCVDZFEWAWHD-GIKRAICYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside 在 4 A molecular sieve 、 四氟化钛 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 17.75h， 生成 Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-4-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  弗氏志贺氏菌血清型5A O-抗原的三糖，四糖和五糖片段的甲基糖苷的线性合成

  摘要：

  甲基α-D-吡喃葡萄糖基-（1→3）-α-L-鼠李吡喃糖基-（1→3）-α-L-鼠李糖吡喃糖苷（EBC-OMe，1），甲基α-L-鼠李糖吡喃糖基-（ 1→2）-[α-D-吡喃葡萄糖基-（1→3）]-α-L-鼠李吡喃糖基-（1→3）-α-L-鼠李吡喃糖苷（A（E）BC-OMe，2）和甲基2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基-（1→2）-α-L-鼠李吡喃糖基-（1→2）-[α-D-吡喃葡萄糖基-（1→3）]-α-L-描述了鼠李糖吡喃糖基-（1→3）-α-L-鼠李糖吡喃糖苷（DA（E）BC-OMe，3）。化合物1、2和3构成弗氏志贺氏菌血清型5a的O-特异性多糖的片段的甲基糖苷。甲基2,4-二-O-苯甲酰基-α-L-鼠李糖基-（1→3）-2,4-二-O-苯甲酰基-α-L-鼠李糖吡喃糖苷是合成1的合适BC前体。为了合成支链目标2和3，苄基最适合于鼠李糖C的2位。因此，甲基4 - O-苄基-

  DOI：

  10.1080/07328300008544096
• 作为产物：
  描述：

  methyl 3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside 在 Wilkinson's catalyst 三乙烯二胺 、 4 A molecular sieve 、 sodium 、 氰化汞 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 46.0h， 生成 methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  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

  摘要：

  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).

  DOI：

  10.1016/s0040-4020(01)80018-1

文献信息

• Synthesis of a Trisaccharide and a Tetrasaccharide from the Cell-Wall Lipopolysaccharides of Azospirillum brasilense S17
  作者：Anup Misra、Shashi Pandey、Samir Ghosh

  DOI：10.1055/s-0029-1217401

  日期：2009.8

  A trisaccharide containing a d-mannosamine moiety and a tetrasaccharide containing an l-rhamnan chain that are found in the cell walls of Azospirillum brasilense S17 were synthesized concisely and in excellent yields. The key features of the synthetic strategy were stereoselective glycosylations and a minimum number of protecting-group manipulations. oligosaccharides - glycosylations - d-mannosamine

  简明地并且以优异的产率合成了在d.Asilspirillum brasilense S17的细胞壁中发现的包含d-甘露糖胺部分的三糖和包含1 - rhamnan链的四糖。合成策略的关键特征是立体选择性糖基化和最少数量的保护基操纵。 低聚糖-糖基化- d -mannosamine -巴西固氮螺菌-根瘤菌
• 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).
• Linear Synthesis of The Methyl Glycosides of Tri-, Tetra-, and Pentasaccharide Fragments of The<i>Shigella Flexneri</i>Serotype 5A<i>O</i>-Antigen
  作者：Laurence A. Mulard、Joël Ughetto-Monfrin

  DOI：10.1080/07328300008544096

  日期：2000.1

  3) is described. Compounds 1, 2 and 3 constitute the methyl glycosides of fragments of the O-specific polysaccharide of Shigella flexneri serotype 5a. Methyl 2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside was an appropriate BC precursor for the synthesis of 1. For the synthesis of the branched targets 2 and 3, a benzyl group was best suited at position 2 of rhamnose

  甲基α-D-吡喃葡萄糖基-（1→3）-α-L-鼠李吡喃糖基-（1→3）-α-L-鼠李糖吡喃糖苷（EBC-OMe，1），甲基α-L-鼠李糖吡喃糖基-（ 1→2）-[α-D-吡喃葡萄糖基-（1→3）]-α-L-鼠李吡喃糖基-（1→3）-α-L-鼠李吡喃糖苷（A（E）BC-OMe，2）和甲基2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基-（1→2）-α-L-鼠李吡喃糖基-（1→2）-[α-D-吡喃葡萄糖基-（1→3）]-α-L-描述了鼠李糖吡喃糖基-（1→3）-α-L-鼠李糖吡喃糖苷（DA（E）BC-OMe，3）。化合物1、2和3构成弗氏志贺氏菌血清型5a的O-特异性多糖的片段的甲基糖苷。甲基2,4-二-O-苯甲酰基-α-L-鼠李糖基-（1→3）-2,4-二-O-苯甲酰基-α-L-鼠李糖吡喃糖苷是合成1的合适BC前体。为了合成支链目标2和3，苄基最适合于鼠李糖C的2位。因此，甲基4 - O-苄基-