5-acetamido-6,7,9-tri-O-acetyl-4,8-anhydro-1,2,3,5-tetradeoxy-D-glycero-D-ido-non-enitol | 180980-29-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-6,7,9-tri-O-acetyl-4,8-anhydro-1,2,3,5-tetradeoxy-D-glycero-D-ido-non-enitol
• 英文别名: 3-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)propene；3-C-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1-propene；[(2R,3S,4R,5S,6S)-5-acetamido-3,4-diacetyloxy-6-prop-2-enyloxan-2-yl]methyl acetate
• CAS: 180980-29-4
• 化学式: C₁₇H₂₅NO₈
• 分子量: 371.387
• InChiKey: OOXMXCKVYWWEGG-DMRKSPOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-acetamido-6,7,9-tri-O-acetyl-4,8-anhydro-1,2,3,5-tetradeoxy-D-glycero-D-ido-non-enitol 在 臭氧 、 三苯基膦 、 lithium diisopropyl amide 作用下， 反应 4.92h， 生成 (Z)-2-tert-Butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-but-2-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of the C-Analog of 2-Acetylamino-2-deoxy-β-d-glucopyranosyl l- and d-Serine

  摘要：

  DOI：

  10.1055/s-1998-4490
• 作为产物：
  描述：

  3-C-(3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-1-propene 生成 5-acetamido-6,7,9-tri-O-acetyl-4,8-anhydro-1,2,3,5-tetradeoxy-D-glycero-D-ido-non-enitol
  参考文献：
  名称：

  Synthesis of β-C-Glycosides of N-Acetylglucosamine via Keck Allylation Directed by Neighboring Phthalimide Groups

  摘要：

  DOI：

  10.1021/jo960819o

文献信息

• Stereocontrolled allylation of 2-amino-2-deoxy sugar derivatives by a free-radical procedure11For preliminary reports on this work, see ref[1].
  作者：Jingrong Cui、Derek Horton

  DOI：10.1016/s0008-6215(98)00141-4

  日期：1998.6

  2-trifluoroacetamido analogue 8 of 4 in 60% yield. The free amino analogue 7 of 4 was conveniently obtained via the 2- p -methoxybenzylideneamino 1-bromide analogue of 1 . Use of 3,4,6-tri- O -acetyl-2-deoxy-2-phthalimido- β - d -glucopyranosyl bromide as radical precursor allowed stereospecific access to β -1- C -allyl derivatives of the amino sugar. The crystalline galactosamine analogue 12 of 4 was obtained

  摘要在对各种N-取代基和糖苷配基作为糖基自由基前体的比较研究中，已评估了2-氨基-2-脱氧糖的异源特异性1- C-烯丙基化的制备途径，该方法可有效捕获烯丙基三丁基锡中的烯丙基。当2-乙酰氨基-3,4,6-tri-O-时，以70％的收率获得3-（2-乙酰氨基-2-脱氧-α-d-吡喃葡萄糖基）-1-丙烯的三乙酸酯晶体4。在自由基条件下，用烯丙基三丁基锡处理乙酰基-2-脱氧-α-d-吡喃葡萄糖基氯（1），而相应的溴化物3仅生成恶唑烷衍生物。1的β-1-乙基黄原酸酯类似物给出4，但收率仅为25％。1的2-三氟乙酰酰胺基1-溴化物类似物也是有效的自由基来源，以60％的收率得到2-三氟乙酰氨基类似物8​​为4。经由4的2-对甲氧基苄叉亚氨基1-溴化物类似物方便地获得4的游离氨基类似物7。使用3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-d-吡喃葡萄糖基溴化物作为自由基前体可以立体定向
• A Short and Economical Synthesis of Orthogonally Protected <i>C</i>-Linked 2-Deoxy-2-acetamido-α-<scp>d</scp>-galactopyranose Derivatives
  作者：Vincent R. Bouvet、Robert N. Ben

  DOI：10.1021/jo051938j

  日期：2006.4.1

  A short and high-yielding synthesis has been devised to prepare C-linked 2-deoxy-2-acetamido-α-d-galactopyranose derivative 3. One of the main advantages of this approach is that it employs commercially available and inexpensive d-glucosamine as the starting material. The key steps include a highly stereoselective C-allylation followed by epimerization of the C-4 hydroxyl group. Building block 3 and

  已经设计了短而高产的合成物来制备C-连接的2-脱氧-2-乙酰氨基-α- d-吡喃半乳糖衍生物3。该方法的主要优点之一是，它使用可商购的和廉价的d-葡糖胺作为起始原料。关键步骤包括高度立体选择性的C-烯丙基化，接着是C -4羟基的差向异构化。结构单元3和受正交保护的C键联的2-脱氧-2-乙酰氨基-α- d-吡喃半乳糖衍生物2分别以44％的总收率（六步）和29％的总收率（八步）获得产物。这代表了对先前报道的合成的重大改进。
• Oxidation of 3-C-(2-amino-2-deoxy-d-glucopyranosyl)-1-propene compounds and the structure of 3-C-(2-amino-2-deoxy-d-glucopyranosyl)-1,2-propanediol derivatives for a synthesis of 2,3-didehydro-2,7-dideoxy-N-acetylneuraminic acid
  作者：Tomoya Machinami、Yasuyuki Itaba、Ayumi Kayama、Takashi Fujimoto、Tetsuo Suami

  DOI：10.1016/s0008-6215(02)00225-2

  日期：2002.11

  Oxidation of 5-acetamido-4,8-anhydro-1,2,3,5-tetradeoxy-D-glycero-D-ido-non-1-enitol [3-C-(2-amino-2-deoxy-beta-D-glucopyranosyl)-1-propene] was studied to search for preparative routes to aminodeoxy didehydro nonulosonic acid derivatives. Since only moderate chiral induction was observed with osmium tetroxide dihydroxylation as well as with peracid epoxidation, the catalytic asymmetric dihydroxylation

  5-乙酰氨基-4,8-​​脱水-1,2,3,5-四脱氧-D-甘油-D-基-非-1-烯醇的氧化[3-C-（2-氨基-2-脱氧-β -D-吡喃葡萄糖基）-1-丙烯]的研究以寻找制备氨基脱氧二氢壬基磺酸衍生物的途径。由于四氧化二羟基化以及过酸环氧化仅观察到中等程度的手性诱导，因此采用催化不对称二羟基化条件以立体控制形成1，2-丙二醇衍生物。这些非对映异构的1,2-丙二醇衍生物的结构通过X射线晶体学分析确定。非对映异构的1,2-丙二醇的形成也随氨基双糖基糖基部分上的2-取代基的性质而变化。因此5-acetamido-4,8-​​anhydro-3，主要得到至多70个的5-二脱氧-D-赤型-L-氨基-壬醇[（2S）-3-C-（2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）-1,2-丙二醇]通过使用ADmixbeta试剂从3-C-（2-乙酰胺基-2-脱氧糖基）-1-丙烯中得到1％的化合物。将（2S）-丙二醇衍生物按五步反应顺序转化为2
• Selective Cross‐Metathesis of<i>C</i>‐Allyl‐Glycosides
  作者：Mattie S. M. Timmer、Marta Vinciano Chumillas、Wilma E. Donker‐Koopman、Johannes M. F. G. Aerts、Gijsbert A. van derMarel、Herman S. Overkleeft、Jacques H. van Boom

  DOI：10.1080/07328300500174887

  日期：2005.8

  The efficient and selective cross-metathesis (CM) of both the alpha- and beta-anomers of C-allyl-glucose and N-acetyl-C-allyl-glucosamine with electron-deficient olefins is reported. The applicability of our CM approach in the synthesis of glycoside-conjugates is illustrated by the CM of alpha-C-allyl-glycosamine 2 with uridinyl vinylphosphonate 22, to produce UDP-GIcNAc analog 23.
• Synthesis of α- and β-C-glycosides of N-acetylglucosamine
  作者：Glenn J. McGarvey、Frank W. Schmidtmann、Tyler E. Benedum、Darin E. Kizer

  DOI：10.1016/s0040-4039(03)00818-9

  日期：2003.5

  As part of efforts to make available new, classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine. (C) 2003 Elsevier Science Ltd. All rights reserved.