3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucal | 63000-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucal
• 英文别名: 3,4,6-tri-O-acetyl-2-phthalimido-D-glucal；3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-2-phthalimido-D-arabino-hex-1-enitol；[(2R,3S,4R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 63000-71-5
• 化学式: C₂₀H₁₉NO₉
• 分子量: 417.372
• InChiKey: HIEIFUJWBCQDQF-KZNAEPCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(toluene-4-sulfinyl)-tetrahydro-pyran-4-yl ester 以 甲苯 为溶剂， 以87%的产率得到3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucal
  参考文献：
  名称：

  An efficient method for the preparation of 2-hydroxy- and 2-aminoglycals from glycosyl sulfoxides

  摘要：

  A new and efficient route to 2-hydroxy- and 2-aminoglycals from glycosyl sulfoxides has been developed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00555-5

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
• Elimination reactions of glycosyl selenoxides
  作者：David J. Chambers、Graham R. Evans、Antony J. Fairbanks

  DOI：10.1016/j.tet.2004.07.005

  日期：2004.9

  Glycosyl selenoxides, generated in situ from selenoglycosides by a Sharpless-type oxidation, undergo facile syn elimination leading to 2-hydroxy and 2-amino glycals in high yield.

  糖苷亚硒酸酯是通过Sharpless型氧化从硒代糖苷原位生成的，可以轻松地进行syn消除，从而以高收率得到2-羟基和2-氨基糖基。
• Synthesis of the Sda determinant and two analogous tetrasaccharides
  作者：Paul B. van Seeventer、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0008-6215(97)00013-x

  日期：1997.4

  To contribute to the possibility of studying in greater detail the biological significance of Sd(a)-containing glycans as occur in Tamm-Horsfall glycoprotein, the following three spacer-linked tetrasaccharides have been synthesized: the Sd(a) determinant alpha-Neup5Ac-(2 --> 3)-[beta D-GalpNAc-(1 --> 4)]-beta-D-Galp-(1 --> 4)-beta-D-GlcpNAc-(1 --> 0)(CH2)(5)NH2 (1), the Gal-analogue alpha-Neup5Ac-(2 --> 3)-[beta-D-Galp-(1 --> 4)]-beta-D-Galp-(1 --> 4)-beta-D-GlcpNAc-(1 --> 0)(CH2)(5)NH2 (2), and the GlcNAc-analogue alpha-Neup5Ac-(2 --> 3)-[beta-D-GlcpNAc-(1 --> 4)]-beta-D-Galp-(1 --> 4)-beta-D-GlcpNAc-(1 --> 0)(CH2)(5)NH2 (3). The general trisaccharide acceptor 5-azidopentyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosylonate)-(2 --> 3)-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside was prepared, using methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-non-2-ulopyranosid)-onate as the sialyl donor. For the syntheses of 1, 2, and 3 the glycosyl donors 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-alpha-D-galactopyranosyl bromide, 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide, and 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate, respectively, proved to be the most suitable. (C) 1997 Elsevier Science Ltd.
• Iterative one-pot syntheses of chitotetroses
  作者：Lijun Huang、Zhen Wang、Xiaoning Li、Xin-shan Ye、Xuefei Huang

  DOI：10.1016/j.carres.2006.01.007

  日期：2006.7

  Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of phenyl 6-O-acyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-d-glucopyranoside
  作者：Tomoya Ogawa、Satoru Nakabayashi、Kikuo Sasajima

  DOI：10.1016/s0008-6215(00)85587-1

  日期：1981.9