Phosphoric acid (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester dibutyl ester | 208656-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phosphoric acid (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester dibutyl ester
• 英文别名: dibutyl [(2S,3R,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] phosphate
• CAS: 208656-41-1
• 化学式: C₃₅H₄₇O₉P
• 分子量: 642.727
• InChiKey: DPKAYMRGMVTCPC-JSMUHSIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  45
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Phosphoric acid (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester dibutyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 叔丁基二甲硅基三氟甲磺酸酯 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3,4,6-Tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Love; Seeberger, Synthesis, 2001, # 2, p. 317 - 322

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-D-glucal epoxide 、 磷酸二丁酯 以 二氯甲烷 为溶剂， 反应 0.08h， 以88%的产率得到Phosphoric acid (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester dibutyl ester
  参考文献：
  名称：

  An Expeditious Route toStreptococciandEnterococciGlycolipidsViaRing-Opening of 1,2-Anhydrosugars with Protic Acids

  摘要：

  1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly beta-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the beta-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective alpha-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected alpha-diglucosyl glycerol derivative 25, which upon desilylation (-->28), acylation (-->29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.

  DOI：

  10.1080/07328309808002906

文献信息

• An Expeditious Route to<i>Streptococci</i>and<i>Enterococci</i>Glycolipids<i>Via</i>Ring-Opening of 1,2-Anhydrosugars with Protic Acids
  作者：C. M. Timmers、N. C.R. van Straten、G. A. van der Marel、J. H. van Boom

  DOI：10.1080/07328309808002906

  日期：1998.4

  1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly beta-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the beta-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective alpha-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected alpha-diglucosyl glycerol derivative 25, which upon desilylation (-->28), acylation (-->29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.
• Love; Seeberger, Synthesis, 2001, # 2, p. 317 - 322
  作者：Love、Seeberger

  DOI：——

  日期：——