fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose | 142800-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose
• 英文别名: [(2S,3R,4R,5S)-6-fluoro-2-methyl-4,5-bis(phenylmethoxy)oxan-3-yl] benzoate
• CAS: 142800-26-8
• 化学式: C₂₇H₂₇FO₅
• 分子量: 450.507
• InChiKey: FZZJCWMSVHGHJN-IJTSQUAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose 在 甲醇 、 2,6-二叔丁基吡啶 、 4 A molecular sieve 、 四丁基氟化铵 、 氨 、 silver perchlorate 、 sodium 、 溶剂黄146 、 tin(ll) chloride 、 zinc dibromide 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 64.5h， 生成
  参考文献：
  名称：

  Application of Glycals to the Synthesis of Oligosaccharides: Convergent Total Syntheses of the Lewis X Trisaccharide Sialyl Lewis X Antigenic Determinant and Higher Congeners

  摘要：

  Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLe(x) tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation-rearrangement step allows for the use of minimally protected glycosides as the glycosyl accepters. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Le(x) glycal.

  DOI：

  10.1021/ja00112a007
• 作为产物：
  描述：

  甲基-Alpha-L-岩藻糖苷 在 吡啶 、 盐酸 、 四丁基溴化铵 、 溶剂黄146 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 三丁基氧化锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.08h， 生成 fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose
  参考文献：
  名称：

  Application of Glycals to the Synthesis of Oligosaccharides: Convergent Total Syntheses of the Lewis X Trisaccharide Sialyl Lewis X Antigenic Determinant and Higher Congeners

  摘要：

  Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLe(x) tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation-rearrangement step allows for the use of minimally protected glycosides as the glycosyl accepters. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Le(x) glycal.

  DOI：

  10.1021/ja00112a007

文献信息

• Remarkable regioselectivity in the chemical glycosylation of glycal acceptors: a concise solution to the synthesis of sialyl-Lewis X glycal.
  作者：Samuel J. Danishefsky、Jacquelyn Gervay、John M. Peterson、Frank E. McDonald、Koshi Koseki、Takeshi Oriyama、David A. Griffith、Chi Huey Wong、David P. Dumas

  DOI：10.1021/ja00047a077

  日期：1992.10
• Total Syntheses of Tumor-Related Antigens N3:  Probing the Feasibility Limits of the Glycal Assembly Method
  作者：Hyunjin M. Kim、In Jong Kim、Samuel J. Danishefsky

  DOI：10.1021/ja0022730

  日期：2001.1.1

  The total syntheses of two octasaccharide antigens isolated from human milk, 1 and 2, and their corresponding allyl glycosides, 3 and 4, have been achieved by utilizing the glycal method, Convergent assembly of the core hexasaccharides and concurrent introduction of two alpha -L-fucosyl moieties at the late stage of the syntheses provided these complex:carbohydrates in a concise manner. With synthetic material obtained, biological evaluations of these antigens as potential gastrointestinal cancer immunotherapeutic agents have been initiated.
• Application of the Glycal Assembly Method to the Concise Synthesis of Neoglycoconjugates of Ley and Leb Blood Group Determinants and of H-Type I and H-Type II Oligosaccharides
  作者：Samuel J. Danishefsky、Victor Behar、John T. Randolph、Kenneth O. Lloyd

  DOI：10.1021/ja00126a011

  日期：1995.5

  The power of the glycal assembly strategy for reaching Lewis and H-type blood group determinants is demonstrated herein. Three key elements form the basis of the method. Thus, alpha-epoxides derived from galactal cyclic carbonate 13 are produced stereospecifically and are highly effective beta-galactosyl donors. Also, 6-monoprotected glucals can be regiospecifically glycosylated at the C-3 hydroxyl (see 23 + 13 --> 24). Moreover, glycosylation via a glycal epoxide produces a unique C-2 hydroxyl in the product which can be exploited as the acceptor site for branching (see formation of 26).
• Behar, Victor; Danishefsky, Samuel J., Angewandte Chemie, 1994, vol. 106, # 14, p. 1536 - 1538
  作者：Behar, Victor、Danishefsky, Samuel J.

  DOI：——

  日期：——
• Application of Glycals to the Synthesis of Oligosaccharides: Convergent Total Syntheses of the Lewis X Trisaccharide Sialyl Lewis X Antigenic Determinant and Higher Congeners
  作者：Samuel J. Danishefsky、Jacquelyn Gervay、John M. Peterson、Frank E. McDonald、Koshi Koseki、David A. Griffith、Takeshi Oriyama、Stephen P. Marsden

  DOI：10.1021/ja00112a007

  日期：1995.2

  Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLe(x) tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation-rearrangement step allows for the use of minimally protected glycosides as the glycosyl accepters. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Le(x) glycal.