2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-D-葡萄糖酸-1,5-内酯 | 34051-37-1

• 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
• 中文名称: 2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-D-葡萄糖酸-1,5-内酯
• 中文别名: 2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧D葡糖酸-1,5-内酯
• 英文名称: 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lacton
• 英文别名: 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lactone；N-[(3R,4R,5S,6R)-2-oxo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 34051-37-1
• 化学式: C₂₉H₃₁NO₆
• 分子量: 489.568
• InChiKey: AYYVTZOWKSEYAH-BIYDSLDMSA-N

物化性质

• 溶解度：
  可溶于丙酮、二氯甲烷、DMSO、

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：

  2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-D-葡萄糖酸-1,5-内酯 在 palladium on activated charcoal 吡啶 、 正丁基锂 、 1,4-环己二烯 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 78.08h， 生成 (Z)-3-acetamido-4,5,7-tri-O-acetyl-2,6-anhydro-1,3-dideoxy-1-dimethoxyphosphoryl-D-gluco-hept-1-enitol
  参考文献：
  名称：

  新型UDP-Glycal衍生物作为UDP-GlcNAc 2-表异构酶的过渡态类似抑制剂

  摘要：

  UDP-GlcNAc 2-epimerase催化将唾液酸生物合成过程中的第一步从UDP-GlcNAc到ManNAc的“表位化”。在本文中，我们报告了该酶基于过渡态抑制剂的合成。为了模拟该反应的假定的第一过渡态（TS 1），我们设计并合成了新型UDP-外糖基衍生物1-4。我们在此还报告了5和6的合成，2-乙酰氨基葡糖的第一个C-糖苷衍生物以及酮苷7和8的合成，它们分别被设计为双底物类似物和双产物类似物，以模拟通过假定的第二过渡态TS 2进行反应的第二步。

  DOI：

  10.1021/jo0353029
• 作为产物：
  描述：

  (2R,3S,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylselanyloxan-3-amine 在 吡啶 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 3 A molecular sieve 、 mercury(II) trifluoroacetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-D-葡萄糖酸-1,5-内酯
  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

• The oxidation of partially substituted 2-acetamido-2-deoxyaldoses with methyl sulfoxideacetic anhydride. Some 2-acetamido-2-deoxyaldonic acid derivatives
  作者：N. Pravdić、H.G. Fletcher

  DOI：10.1016/s0008-6215(00)86165-0

  日期：1971.10

  Abstract The oxidation of 2-acetamido-3,4,6-tri- O -benzyl-2-deoxy- d -glucopyranose ( 1 ) by methyl sulfoxide-acetic anhydride gave crystalline 2-acetamido-3,4,6-tri- O -benzyl-2-deoxy- d -glucono-1,5-lactone ( 2 ) in high yield. Debenzylation of 2 yielded 2-acetamido-2-deoxy- d -glucono-1,5-lactone ( 3 ). The reaction of 2 with methanol gave methyl 2-acetamido-3,4,6-tri- O -benzyl-2-deoxy- d -gluconate

  摘要甲基亚砜-乙酸酐氧化2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-d-吡喃葡萄糖（1），得到2-乙酰氨基-3,4,6-三-结晶。 O-苄基-2-脱氧-d-葡萄糖基-1,5-内酯（2）高产。2的脱苄基作用产生2-乙酰氨基-2-脱氧-d-葡萄糖基-1，5-内酯（3）。2与甲醇的反应得到2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-d-葡萄糖酸甲酯（4），然后将该化合物脱苄基，得到游离酯（5）。与二甲胺一起，由2-乙酰氨基-2-脱氧-d-甘露糖醇-1,4-内酯（6）生成结晶的二-N-甲基酰胺（7），也可以通过将相同的试剂作用于二甲胺的混合物上而获得。通过将2-乙酰氨基-2-脱氧-d-葡萄糖与无缓冲溴水溶液氧化得到的化合物。由于7可以转换回6，认为这两种化合物具有相同的构型。与二甲胺一起，内酯2得到两种2-乙酰氨基-3,4,6-O-苄基-2-脱氧-二-N-甲基己二酰胺（8和9）的混合物
• 1,5-Dideoxy-1,5-imino-D-glucitol Compounds
  申请人：Lin Chun-Hung

  公开号：US20100113519A1

  公开（公告）日：2010-05-06

  1,5-Dideoxy-1,5-imino-D-glucitol compounds as shown in the specification. Also disclosed is a method of treating a hexosaminidase-associated disease.

  规范中显示的1,5-二去氧-1,5-亚胺-D-葡萄糖醇化合物。还公开了一种治疗己糖氨基酸酶相关疾病的方法。
• Synthesis and Some Transformations of 2-Acetamido-5-amino-3,4,6-tri-O-benzyl-2,5-dideoxy-D-glucono-1,5-lactam
  作者：Thierry Granier、Andrea Vasella

  DOI：10.1002/hlca.19980810508

  日期：——

  yield of 72% from the hydroxy amide 16 by oxidation with the Dess-Martin periodinane, acid-catalysed isomerization of the oxidation products in toluene, whereupon 18/19 precipitated, and reductive dehydroxylation of 18/19 (Et3SiH/BF3 · OEt2; Scheme 1). The amide 16 was obtained by ammonolysis of the N-acetylglucosamine-derived lactone 15. Depending on the oxidation method, 16 yielded the keto amide 17,

  内酰胺21中的72％从所述羟基酰胺的总产率得到16与通过氧化戴斯-马丁高碘剂，氧化产物在甲苯中的酸催化的异构化，随后18 / 19析出，的还原性脱18 / 19（Et 3 SiH / BF 3 ·OEt 2；方案1）。酰胺16通过对N-乙酰基葡糖胺衍生的内酯15进行氨解而获得。取决于氧化方法，16得到的酮酰胺17中，羟基内酰胺18 / 19，和吡咯烷甲酰胺20在广泛不同的比例。吡咯烷羧酰胺20在还原性脱羟基的条件下不被还原。苄基保护的内酰胺21的氢解产生三羟基内酰胺22，同时用NaBH 4 / BF 3 ·OEt 2还原产生2-乙酰氨基哌啶衍生物24（方案2）。内酰胺21（25的选择性（叔丁氧基）羰基化），随后加入NaBH 4还原和在EtOH酸催化溶剂分解导致α-ethoxycarbamates 28 / 29日。类似地，（叔丁氧基）羰基的1（31），随后还原至32 / 33和苷化，得到乙
• 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.