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3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose | 132183-13-2

中文名称
——
中文别名
——
英文名称
3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose
英文别名
3,4,6-Tri-O-acetyl-2-azido-2-desoxy-β-D-galactopyranose;3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranose;3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactose;(2R,3R,4R,5R)-2-(acetoxymethyl)-5-azido-6-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate;2-azido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranose;3,4,6-tri-O-acetyl-2-deoxy-2-azido-D-galactopyranose;[(2R,3R,4R,5R,6R)-3,4-diacetyloxy-5-azido-6-hydroxyoxan-2-yl]methyl acetate
3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose化学式
CAS
132183-13-2
化学式
C12H17N3O8
mdl
——
分子量
331.282
InChiKey
PLVPDCSPQJIUQM-RMPHRYRLSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    0.1
  • 重原子数:
    23
  • 可旋转键数:
    8
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.75
  • 拓扑面积:
    123
  • 氢给体数:
    1
  • 氢受体数:
    10

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    A highly stereoselective synthesis of di- and trimeric sialosyltn epitope: A partial structure of glycophorin A
    摘要:
    DOI:
    10.1016/s0040-4039(00)97201-0
  • 作为产物:
    描述:
    3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl acetate碳酸氢铵 作用下, 以 四氢呋喃甲醇 为溶剂, 以78%的产率得到3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose
    参考文献:
    名称:
    Synthesis and immunological study of a wall teichoic acid-based vaccine against E. faecium U0317
    摘要:
    A repeat unit of cell wall teichoic acids (WTA) isolated from E. faecium U0317 was chemically synthesized efficiently by a stepwise strategy. It was derivatized with a 5-aminopentanyl linker to facilitate conjugation with carrier proteins KLH and HSA. Immunological studies of the KLH conjugate 1 demonstrated that it could provoke robust immune responses and high titers of IgG antibodies, which could successfully recognize the synthesized WTA repeat unit 3. This result suggested that synthetic glycoconjugate 1 could be a promising vaccine candidate against E. faecium for further studies.
    DOI:
    10.1080/07328303.2017.1390576
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文献信息

  • Use of Hydrazine Acetate as a Mild and Efficient Reagent for Anomeric Denitration of Carbohydrates
    作者:Tatsushi Toyokuni、Shaopei Cai、Barbara Dean
    DOI:10.1055/s-1992-26347
    日期:——
    Treatment of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α,β-D-galactopyranosyl nitrate (1), 3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4, 6-tetra-O-acetyl-β-D-galactopyranosyl)-α,β-D-glucopyranosyl nitrate (3), and 6-O-acetyl-2-azido-2-deoxy-3,4-O-isopropylidene-α,β-D-galactopyranosyl nitrate (5) with a slight excess of hydrazine acetate in anhydrous dimethylformamide at room temperature for 2 hours gave the corresponding hemiacetals, 2, 4, and 6 in the range of an 87-92 % yield.
    将 3,4,6-三-O-乙酰基-2-叠氮-2-脱氧-δ±,δ-D-喃半乳糖硝酸酯 (1)、3,6-二-O-乙酰基-2-叠氮-2-脱氧-4-O-(2,3,4, 6-四-O-乙酰基-δ-D-喃半乳糖基)-δ±,δ-D-吡喃葡萄糖硝酸酯 (3) 和 6-O-乙酰基-2-叠氮-2-脱氧-3、在室温下,在无二甲基甲酰胺中加入稍过量的乙酸 2 小时,再加入 4-O-异亚丙基-δ,δ-D-喃半乳糖硝酸酯(5),得到相应的半乙酸酯 2、4 和 6,收率范围为 87-92%。
  • Efficient Synthesis of Azido Sugars Using Fluorosulfuryl Azide Diazotransfer Reagent**
    作者:Joshua M. Kofsky、Gour C. Daskhan、Matthew S. Macauley、Chantelle J. Capicciotti
    DOI:10.1002/ejoc.202200108
    日期:2022.8.5
    An operationally simple protocol for diazotransfer on amine-containing carbohydrates has been developed. This high-yielding reaction can be conducted under ambient conditions. Reaction completion is indicated by the colour change of the Cu(II) catalyst. The utility of this protocol in chemical glycosylation has been demonstrated through the preparation of azide-containing glycosyl donors with orthogonal
    已开发出一种操作简单的含胺碳水化合物重氮转移方案。这种高产反应可以在环境条件下进行。反应完成由 Cu(II) 催化剂的颜色变化指示。该协议在化学糖基化中的效用已通过制备具有正交保护基团的含叠氮化物糖基供体得到证明。
  • Stereoselective entry into the d-GalNAc series starting from the d-Gal one: a new access to N-acetyl-d-galactosamine and derivatives thereof
    作者:Lorenzo Guazzelli、Giorgio Catelani、Felicia D’Andrea、Alessia Giannarelli
    DOI:10.1016/j.carres.2008.11.018
    日期:2009.2
    A new stereoselective preparation of N-aceyl-D-galactosamine (1b) starting from the known p-methoxyphenyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-beta-D-galactopyranoside (10) is described using a simple strategy based on (a) epimerization at C-2 of 10 via oxidation-reduction to give the talo derivative 11, (b) amination with configurational inversion at C-2 of 11 via a S(N)2-type reaction
    从已知的对甲氧基苯基3,4-O-异亚丙基-6-O-(1-甲氧基-1-甲基乙基)-β-D-喃半乳糖苷(使用基于(a)通过氧化还原在C-2处10的差向异构化得到滑石生物11(b)通过S(N)在C-2处11的构型反转的胺化的简单策略来描述10)在其2-亚酰胺基上进行2型反应,(c)对甲氧基苯基β-D-半乳糖胺糖苷14的端基异构脱保护,(d)完全脱保护。将相同的方法应用于通过以下方法直接获得的2,3:5,6:3',4'-三-O-异亚丙基-6'-O-(1-甲氧基-1-甲基乙基)-乳糖二甲基乙缩醛(4)乳糖的乙酰化,二糖β-D-GalNAcp-(1->
  • Synthesis of peptides and glycopeptides with polyproline II helical topology as potential antifreeze molecules
    作者:Leo Corcilius、Gajan Santhakumar、Robin S. Stone、Chantelle J. Capicciotti、Soumya Joseph、Jacqueline M. Matthews、Robert N. Ben、Richard J. Payne
    DOI:10.1016/j.bmc.2013.02.025
    日期:2013.6
    A library of peptides and glycopeptides containing (4R)-hydroxy-L-proline (Hyp) residues were designed with a view to providing stable polyproline II (PPII) helical molecules with antifreeze activity. A library of dodecapeptides containing contiguous Hyp residues or an Ala-Hyp-Ala tripeptide repeat sequence were synthesized with and without alpha-O-linked N-acetylgalactosamine and a-O-linked galactose-beta-(1 -> 3)-N-acetylgalactosamine appended to the peptide backbone. All (glyco) peptides possessed PPII helical secondary structure with some showing significant thermal stability. The majority of the (glyco) peptides did not exhibit thermal hysteresis (TH) activity and were not capable of modifying the morphology of ice crystals. However, an unglycosylated Ala-Hyp-Ala repeat peptide did show significant TH and ice crystal re-shaping activity suggesting that it was capable of binding to the surface of ice. All (glyco) peptides synthesized displayed some ice recrystallization inhibition (IRI) activity with unglycosylated peptides containing the Ala-Hyp-Ala motif exhibiting the most potent inhibitory activity. Interestingly, although glycosylation is critical to the activity of native antifreeze glycoproteins (AFGPs) that possess an Ala-Thr-Ala tripeptide repeat, this same structural modification is detrimental to the antifreeze activity of the Ala-Hyp-Ala repeat peptides studied here. (C) 2013 Elsevier Ltd. All rights reserved.
  • One-Step TEMPO-Catalyzed and Water-Mediated Stereoselective Conversion of Glycals into 2-Azido-2-deoxysugars with a PIFA–Trimethylsilyl Azide Reagent System
    作者:Ande Chennaiah、Yashwant D. Vankar
    DOI:10.1021/acs.orglett.8b00814
    日期:2018.5.4
    An unprecedented water-mediated and TEMPO-catalyzed, one-step, highly regiospecific and stereoselective functionalization of glycals to 2-azido-2-deoxysugars has been developed using a PIFA-Me3SiN3 reagent system in the presence of Bu4NHSO4 as a phase-transfer catalyst. The method is metal-free, proceeds under mild reaction conditions, and tolerates a variety of protecting groups. Using this method, the synthesis of an important trisaccharide unit bound by the monoclonal anti-I Ma antibody has also been demonstrated.
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