benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-<(R)-1-carboxyethyl>-2-deoxy-α-D-glucopyranoside | 123418-19-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-<(R)-1-carboxyethyl>-2-deoxy-α-D-glucopyranoside
• 英文别名: (2R)-2-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxypropanoic acid
• CAS: 123418-19-9
• 化学式: C₃₃H₄₄N₂O₁₃
• 分子量: 676.718
• InChiKey: JTTFHEZVJVKWPZ-QAYPXEQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  212
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-<(R)-1-carboxyethyl>-2-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal Woodward reagent K 、 氢气 、 三乙胺 作用下， 以 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-glucopyranose
  参考文献：
  名称：

  Convenient syntheses of O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→6 and 4)-N-acetylmuramoyl-l-alanyl-d-isoglutamine

  摘要：

  Catalytic hydrogenation of N-{2-O-[benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-.beta.-D-glucopyranosyl)-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine tert-butyl ester (1) afforded N-{2-O-[2-acetamido-6-O-(2-acetamido-2-deoxy-.beta.-D-glucopyranosyl)-2,3-dideoxy-D-glucopyranos-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine tert-butyl ester (2). Carboxyl-deprotection of 1 with trifluoroacetic acid gave N-{2-O-[benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-.beta.-D-glucopyranosyl)-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine (3), which, on hydrogenolysis, afforded the title (1.fwdarw.6)-linked disaccharide-dipeptide 4. Coupling of benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-.beta.-D-glucopyranosyl)-6-O-benzyl-3-O-[(R)-1-carboxyethyl]-2-deoxy-.alpha.-D-glucopyranoside (6) with the benzyl ester of L-alanyl-D-isoglutamine gave N-{-2-O-[benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-.beta.-D-glucopyranosyl)-6-O-benzyl-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine benzyl ester (7). O-Deacetylation of 7 in basic media was accompanied by .alpha..fwdarw..gamma. transamidation reaction at the isoglutaminyl residue. Coupling of the O-deacetylated derivative (8) of 6 with the dipeptide benzyl ester yielded N-{2-O-[benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-.beta.-D-glucopyrano-syl)-6-O-benzyl-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine benzyl ester (9) having HO-3'',4'',6'' unsubstituted. Catalytic hydrogenation of 9 afforded the title (1.fwdarw.4)-linked disaccharide-dipeptide 10.

  DOI：

  10.1016/0008-6215(89)84006-6
• 作为产物：
  描述：

  benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-α-D-glucopyranoside 在 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以90%的产率得到benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-<(R)-1-carboxyethyl>-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Convenient syntheses of O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→6 and 4)-N-acetylmuramoyl-l-alanyl-d-isoglutamine

  摘要：

  Catalytic hydrogenation of N-{2-O-[benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-.beta.-D-glucopyranosyl)-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine tert-butyl ester (1) afforded N-{2-O-[2-acetamido-6-O-(2-acetamido-2-deoxy-.beta.-D-glucopyranosyl)-2,3-dideoxy-D-glucopyranos-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine tert-butyl ester (2). Carboxyl-deprotection of 1 with trifluoroacetic acid gave N-{2-O-[benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-.beta.-D-glucopyranosyl)-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine (3), which, on hydrogenolysis, afforded the title (1.fwdarw.6)-linked disaccharide-dipeptide 4. Coupling of benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-.beta.-D-glucopyranosyl)-6-O-benzyl-3-O-[(R)-1-carboxyethyl]-2-deoxy-.alpha.-D-glucopyranoside (6) with the benzyl ester of L-alanyl-D-isoglutamine gave N-{-2-O-[benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-.beta.-D-glucopyranosyl)-6-O-benzyl-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine benzyl ester (7). O-Deacetylation of 7 in basic media was accompanied by .alpha..fwdarw..gamma. transamidation reaction at the isoglutaminyl residue. Coupling of the O-deacetylated derivative (8) of 6 with the dipeptide benzyl ester yielded N-{2-O-[benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-.beta.-D-glucopyrano-syl)-6-O-benzyl-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine benzyl ester (9) having HO-3'',4'',6'' unsubstituted. Catalytic hydrogenation of 9 afforded the title (1.fwdarw.4)-linked disaccharide-dipeptide 10.

  DOI：

  10.1016/0008-6215(89)84006-6

文献信息

• KANTOCI, DARKO;KEGLEVIC, DINA;DEROME, ANDREW E., CARBOHYDR. RES., 186,(1989) N, C. 77-85
  作者：KANTOCI, DARKO、KEGLEVIC, DINA、DEROME, ANDREW E.

  DOI：——

  日期：——