2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-galactono-1,5-lactone | 176169-12-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-galactono-1,5-lactone
• 英文别名: N-[(3R,4R,5R,6R)-2-oxo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 176169-12-3
• 化学式: C₂₉H₃₁NO₆
• 分子量: 489.568
• InChiKey: AYYVTZOWKSEYAH-ZZXHUEHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三甲基铝 、 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-galactono-1,5-lactone 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以85%的产率得到N-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-2-methyl-tetrahydro-pyran-3-yl)-acetamide
  参考文献：
  名称：

  Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

  摘要：

  Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of Methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected I-C-Me GlcNAc oxazoline, a potential I-C-Me GlcNAc donor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01506-x
• 作为产物：
  描述：

  2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-D-galactopyranose 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-galactono-1,5-lactone
  参考文献：
  名称：

  Convenient Preparation of Perbenzylated 2-Azido and 2-N-Acetylamino-2-Deoxy-d-Hexono-1,5-Lactones by Oxidation of the Corresponding Lactols

  摘要：

  2-Azido-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (1, 2, 3) were oxidized with DMSO in the presence of acetic anhydride. From 1 and 2 the corresponding lactone derivatives were obtained in good yield (89-92%), whereas from 3, glucono-1,5-lactone was obtained (92%) after complete epimerization at C-2. 2-N-Acetylamino-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (7, 8, 9) were obtained from the corresponding 2-azido phenylselenoglycopyranosides (13, 14, 15) by reduction, N-acetylation and hydrolysis catalyzed by mercury trifluoroacetate. Oxidation of 7 and 8 by tetra-n-propylammonium tetra-oxoruthenate (VII) in the presence of 4-methylmorpholine-N-oxide afforded the corresponding lactones in good yield (90%) and high purity. Epimerization at C-2 occurred during oxidation of 9 and perbenzylated D-glucono-1,5-lactone (11) was obtained (90%).

  DOI：

  10.1080/07328309608005438

文献信息

• Alkylidenation of Sugar Lactones and Further Transformation to<i>C</i>-Glycosides
  作者：Juan Xie、Adeline Molina、Stanislas Czernecki

  DOI：10.1080/07328309908544013

  日期：1999.1

  The Wittig reaction of (carbethoxymethylene)triphenylphosphorane with perbenzylated sugar delta-lactones and their 2-acetamido-2-deoxy derivatives is described. It is shown that this olefination occurred readily with the galacto and gluco derivatives, leading stereoselectively to Z-C-glycosylidenes in good yields. However, the same reaction with the perbenzylated 2-deoxy-D-arabino-hexono-1,5-lactone and the mannonolactones worked poorly. Reduction over Pd/C followed by acetylation of the obtained C-glycosylidenes led stereoselectively to peracetylated beta-C-glycosides and amino beta-C-glycosides. The olefin function could also be reduced selectively by Raney nickel or NiCl2/NaBH4, affording the perbenzylated C-glycosides and amino beta-C-glycosides. Other transformation of the enol ether function is also reported.
• Stereocontrolled synthesis of β-C-glycosides and amino β-C-glycosides by Wittig olefination of perbenzylated glyconolactones derivatives
  作者：Adeline Molina、Stanislas Czernecki、Juan Xie

  DOI：10.1016/s0040-4039(98)01627-x

  日期：1998.10

  Wittig olefination of perbenzylated glyconolactones afforded stereoselectively the Z-C-glycosylidenes which were transformed to the corresponding beta-C-glycosides and amino beta-C glycosides by hydrogenation followed by acetylation. (C) 1998 Elsevier Science Ltd. All rights reserved.
• General, stereoselective synthesis of ethylene isosteres of α- and β-glycosylasparagines
  作者：Alessandro Dondoni、Giandomenico Mariotti、Alberto Marra

  DOI：10.1016/s0040-4039(00)00403-2

  日期：2000.4

  The coupling of alpha- or beta-D-linked lithium C-glycosyl acetylides with N-Boc D-serinal acetonide followed by the reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring afforded alpha- and beta-anomer pairs of C-glycosyl alpha-aminopentanoic acids (gluco, manno, galacto, and 2-acetamido-galacto). (C) 2000 Elsevier Science Ltd. All rights reserved.
• Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline
  作者：Spencer Knapp、Chunhua Yang、Thomas Haimowitz

  DOI：10.1016/s0040-4039(02)01506-x

  日期：2002.9

  Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of Methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected I-C-Me GlcNAc oxazoline, a potential I-C-Me GlcNAc donor. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Convenient Preparation of Perbenzylated 2-Azido and 2-<i>N</i>-Acetylamino-2-Deoxy-<scp>d</scp>-Hexono-1,5-Lactones by Oxidation of the Corresponding Lactols
  作者：Ebtissam Ayadi、Stanislas Czernecki、Juan Xie

  DOI：10.1080/07328309608005438

  日期：1996.2

  2-Azido-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (1, 2, 3) were oxidized with DMSO in the presence of acetic anhydride. From 1 and 2 the corresponding lactone derivatives were obtained in good yield (89-92%), whereas from 3, glucono-1,5-lactone was obtained (92%) after complete epimerization at C-2. 2-N-Acetylamino-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (7, 8, 9) were obtained from the corresponding 2-azido phenylselenoglycopyranosides (13, 14, 15) by reduction, N-acetylation and hydrolysis catalyzed by mercury trifluoroacetate. Oxidation of 7 and 8 by tetra-n-propylammonium tetra-oxoruthenate (VII) in the presence of 4-methylmorpholine-N-oxide afforded the corresponding lactones in good yield (90%) and high purity. Epimerization at C-2 occurred during oxidation of 9 and perbenzylated D-glucono-1,5-lactone (11) was obtained (90%).