N-(9-fluorenylmethoxycarbonyl)-O-(3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester | 1381864-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-O-(3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester
• 英文别名: benzyl (2S)-3-[[(2S,4aR,6S,7R,8R,8aR)-8-acetyloxy-7-azido-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 1381864-52-3
• 化学式: C₄₀H₃₈N₄O₁₀
• 分子量: 734.763
• InChiKey: GLMKIBBLUCMBQS-BXSZSDLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-(3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester 在 吡啶 、 高氯酸 、 水 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 benzyl (2S)-3-[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-3-azido-6-[[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-azidooxan-2-yl]oxymethyl]oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures

  摘要：

  TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of alpha-selectivity (alpha/beta=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.059
• 作为产物：
  描述：

  Fmoc-O-苄基-L-丝氨酸 、 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl diphenyl phosphate 在 四氢呋喃 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成 N-(9-fluorenylmethoxycarbonyl)-O-(3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl)-L-serine benzyl ester 、 N-(9-fluorenylmethoxycarbonyl)-O-(3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester
  参考文献：
  名称：

  A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures

  摘要：

  TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of alpha-selectivity (alpha/beta=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.059

文献信息

• A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures
  作者：Kosuke Kakita、Toshifumi Tsuda、Noritoshi Suzuki、Seiichi Nakamura、Hisanori Nambu、Shunichi Hashimoto

  DOI：10.1016/j.tet.2012.04.059

  日期：2012.6

  TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of alpha-selectivity (alpha/beta=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides. (C) 2012 Elsevier Ltd. All rights reserved.