N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester | 337903-73-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester
• 英文别名: N-(9-fluorenylmethoxycarbonyl)-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-serine benzyl ester；benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 337903-73-8
• 化学式: C₃₉H₄₂N₂O₁₃
• 分子量: 746.768
• InChiKey: YFHLTVVKNQMZBT-BXBSBLCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  191
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-serine benzyl ester
  参考文献：
  名称：

  Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

  摘要：

  This work describes the synthesis in Solution of a series of related diketopiperazines with potential biological activities: cyclo(L-Pro-L-Ser), cyclo(L-Phe-L-Ser), cyclo(D-Phe-L-Ser) and the corresponding glycosylated analogs of the latter, cyclo[D-Phe-L-Ser(alpha GlcNAc)] and cyclo[D-Phe-L-Ser(beta GlcNAc)]. The synthetic approach involved coupling reactions of -OH or O-glycosylated serine benzyl esters with NFmoc-protected amino acids (Pro or Phe), followed by one-pot deprotection-cyclization reaction in the presence of 20% piperidine in DMF. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.069
• 作为产物：
  描述：

  2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 4 A molecular sieve 、 氢溴酸 、 silver trifluoromethanesulfonate 、 锌 作用下， 以 吡啶 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 36.0h， 生成 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester
  参考文献：
  名称：

  Solid-Phase Synthesis of O-Linked Glycopeptide Analogues of Enkephalin

  摘要：

  The synthesis of 18 N-alpha -FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-alpha -FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-alpha -FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-beta (1-4)-Gle (lactose), Glc-beta-(1-4)-Glc (cellobiose), and Gal-alpha (1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-PheDCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.

  DOI：

  10.1021/jo005712m

文献信息

• Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-d-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters
  作者：Ivone Carvalho、Shona L Scheuerl、K.P Ravindranathan Kartha、Robert A Field

  DOI：10.1016/s0008-6215(03)00071-5

  日期：2003.5

  Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyla-alpha-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding P-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding beta-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively). (C) 2003 Elsevier Science Ltd. All rights reserved.