methyl (4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranosyl)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate | 311350-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranosyl)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate
• CAS: 311350-25-1
• 化学式: C₄₄H₄₈O₁₂
• 分子量: 768.858
• InChiKey: WUUUIYIXGYBACE-ZLGPERNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  56.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  137.44
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl (4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranosyl)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 在 iodonium(di-γ-collidine) perchlorate 、 sodium acetate 、 palladium dichloride 作用下， 以 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 26.0h， 生成 methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-α-D-galactopyranosyluronate)-(1->2)-(4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranosyl)-(1->4)-(2,3-di-O-benzyl-α-D-galactopyran)uronate
  参考文献：
  名称：

  Synthesis of Rhamnogalacturonan I Fragments

  摘要：

  The partially deprotected trisaccharide 17 has been synthesized as an analogue of the repeating unit of the backbone of rhamnogalacturonan I. The trisaccharide 17 was obtained after prior selective derivatization of HO-3 and HO-4 of a rhamnopyranose cyanoethylidene glycosyl donor, followed by coupling with a tritylated galactopyranosyluronic acceptor (11), selective removal of the acetyl group at the O-2' position of the formed disaccharide 12, and glycosylation of the HO-2' position with methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-beta-D-galactopyranosid)uronate (14) providing methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-alpha-D-galactopyranosyluronate)-(1-->2)-(4-O-benzoyl-3-O-benzyl-alpha-L-rhamnopyranosyl)-(1-->4)-(allyl 2,3-di-O-benzyl-beta-D-galactopyranosid)uronate (15). Finally, palladium chloride catalyzed deallylation (16) and hydrogenolysis over Pd-C resulted in methyl (methyl alpha-D-galactopyranosyluronate)(1-->2)-(4-O-benzoyl-alpha-L-rhamnopyranosyl)-(1-->4)-alpha/beta D-galactopyranuronate (17).

  DOI：

  10.1080/07328300008544126
• 作为产物：
  描述：

  methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以98%的产率得到methyl (4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranosyl)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of Rhamnogalacturonan I Fragments

  摘要：

  The partially deprotected trisaccharide 17 has been synthesized as an analogue of the repeating unit of the backbone of rhamnogalacturonan I. The trisaccharide 17 was obtained after prior selective derivatization of HO-3 and HO-4 of a rhamnopyranose cyanoethylidene glycosyl donor, followed by coupling with a tritylated galactopyranosyluronic acceptor (11), selective removal of the acetyl group at the O-2' position of the formed disaccharide 12, and glycosylation of the HO-2' position with methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-beta-D-galactopyranosid)uronate (14) providing methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-alpha-D-galactopyranosyluronate)-(1-->2)-(4-O-benzoyl-3-O-benzyl-alpha-L-rhamnopyranosyl)-(1-->4)-(allyl 2,3-di-O-benzyl-beta-D-galactopyranosid)uronate (15). Finally, palladium chloride catalyzed deallylation (16) and hydrogenolysis over Pd-C resulted in methyl (methyl alpha-D-galactopyranosyluronate)(1-->2)-(4-O-benzoyl-alpha-L-rhamnopyranosyl)-(1-->4)-alpha/beta D-galactopyranuronate (17).

  DOI：

  10.1080/07328300008544126

文献信息

• Synthesis of rhamnogalacturonan I fragments by a modular design principle
  作者：Navid Nemati、Gnuni Karapetyan、Birte Nolting、Hans-Ulrich Endress、Christian Vogel

  DOI：10.1016/j.carres.2008.03.020

  日期：2008.7

  improved syntheses of methyl 2-O-acetyl-3-O-benzyl-alpha-L-rhamnopyranoside (12) and 1,2-di-O-acetyl-3-O-benzyl-alpha-L-rhamnopyranose (15), which were used as glycosyl acceptor and donor, respectively, are described. Glycosylation of the O-4 position of both rhamnose derivatives with 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl bromide (26) provided disaccharides 27 and 29. After partial deprotection

  改进的甲基2-O-乙酰基-3-O-苄基-α-L-鼠李吡喃糖苷（12）和1,2-二-O-乙酰基-3-O-苄基-α-L-鼠李糖吡喃糖（15）的合成分别描述了分别用作糖基受体和供体的糖苷。两种鼠李糖衍生物的O-4位置被2,3,4,6-四-O-苯甲酰基-α-D-吡喃半乳糖基溴化物糖基化（26），得到二糖27和29。在27的部分脱保护并偶联后，用二糖19得到28，得到四糖31。此外，将29转化为相应的溴化物30并与半乳糖醛酸酯16和32偶联分别提供了三糖33和34，其可以被认为是分支的鼠李糖半乳糖醛酸聚糖片段的结构单元。