methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside | 194347-75-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6S)-5-acetyloxy-2-methyl-6-methylsulfanyl-4-phenylmethoxyoxan-3-yl] benzoate
• CAS: 194347-75-6
• 化学式: C₂₃H₂₆O₆S
• 分子量: 430.522
• InChiKey: NFLQJZKZYPVIKU-SDECBMAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside 在 吡啶 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol
  参考文献：
  名称：

  通过 2-Ulosyl 供体方法有效生成 β-L-鼠李糖苷键：合成具有中心 β-L-鼠李糖单元的三糖

  摘要：

  已经开发了从 L-鼠李糖生产各种封闭的 6-脱氧-α-L-阿拉伯-2-酮己糖基溴化物的实用程序。这些化合物作为间接 β-L-鼠李糖基供体非常有用：它们在 Koenigs-Knorr 条件下进行 β-特异性糖苷化，所得 6-脱氧-β-L-己糖苷糖的 2-酮基被高 β- L-鼠李糖选择性。证明了这种 2-ulosyl 供体方法在合成含 β-L-鼠李糖的二糖和三糖中的直接应用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300149
• 作为产物：
  描述：

  methyl 4-O-benzoyl-1-thio-α-L-rhamnopyranoside 在 氢氧化钾 、 二正丁基氧化锡 作用下， 生成 methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Efficient generation of β-l-rhamnosidic linkages via the ulosyl bromide approach

  摘要：

  Practical protocols have been developed for the acquisition of ulosyl bromides of type III from L-rhamnose, i.e. 6-deoxy-alpha-L-arabino-2-ketohexosyl bromides 6-8. They have high potential as indirect beta-L-rhamnosyl donors, as they undergo beta-specific glycosidations under Koenigs-Knorr conditions, and carbonyl reductions of the resulting beta-L-ulosides proceed with high beta-L-rhamno selectivity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01225-2

文献信息

• BLOCK SYNTHESIS WITH GALACTURONATE TRICHLOROACETIMIDATES1
  作者：Birte Nolting、Hanna Boye、Christian Vogel

  DOI：10.1081/car-100108276

  日期：——

  The disaccharide methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-alpha -L-rhamno pyranosyl)-(1 -->4)-(allyl 2,3-di-O-benzyl-beta -D-galactopyranosid)uronate (13) was obtained in an excellent yield of 88% using methyl (allyl 2,3-di-O-benzyl-beta -D-galactopyranosid)uronate (12) as the glycosyl acceptor and a slight excess Of the 1,2-di-O-acetyl-rhamnoglycosyl donor 5a. Disaccharide 13 is a key intermediate that can be used either as a glycosyl acceptor or glycosyl donor for the preparation of rhamnogalacturonan fragments. Here, introduction of the trichloroacetimidate function at the anomeric center gave the disaccharide glycosyl donor 28, which could be applied in a blockwise glycosylation reaction to form the L-Rha-alpha (1 -->4)-D-GalA-alpha (1 -->4)-D-GalA trisaccharide 29. Generally, on condition that no neighboring group effect influenced the reaction at the anomeric center of the alpha -trichloroacetimidate galacturonate glycosyl donors (20-22,28), alpha -glycosidic linkages were nearly exclusively formed, except in the case of the 4-O-methylgalactopyranosyluronate 22.