2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal | 119827-44-0

• 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-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal
• 英文别名: 2-C-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal；2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylethanal；[(2R,3R,4R,5S,6R)-3,4,5-triacetyloxy-6-(2-oxoethyl)oxan-2-yl]methyl acetate
• CAS: 119827-44-0
• 化学式: C₁₆H₂₂O₁₀
• 分子量: 374.345
• InChiKey: FFERSWWEXDRJFC-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal 在 N-氯代丁二酰亚胺 、 盐酸羟胺 、 sodium acetate 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 (2R,3R,4R,5S,6R)-2-(acetoxymethyl)-6-((Z)-2-(((R)-2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)thio)-2-(hydroxyimino)ethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  通过氯肟-硫醇偶联合成糖偶联物

  摘要：

  引入聚糖是改善治疗性生物分子药理学特性的一种有效化学方法。在此，我们报道了通过氯肟-硫醇偶联物高效合成糖缀合物的方法。衍生自吡喃糖或呋喃糖的反应性糖基氯肟很容易与多种含巯基的底物偶联，包括肽、糖和硫酚。该方法具有反应条件温和、动力学快速的特点。水性介质和克级合成的能力证明了该方法在糖类与生物活性分子的生物偶联中的潜力。

  DOI：

  10.1021/acs.joc.4c00356
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-propene 在 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以90%的产率得到2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal
  参考文献：
  名称：

  尿苷5'-二磷酸葡萄糖的类似物。糖脂生物合成的抑制作用。

  摘要：

  使用羟基苯并三唑方法，用四种不同的磷酸化试剂对2'，3'-O-苯甲酰-尿苷进行磷酸化，得到完全保护的中间体，在加入3,7-脱水-苯甲酰后，该中间体可以转化为UDP-Glc的相应类似物。 4,5,6,8-四-O-乙酰基-2-脱氧-D-赤型-L-古洛糖醇和去除保护基团。

  DOI：

  10.1016/s0040-4039(00)80636-x

文献信息

• Synthesis of C-(d-glycopyranosyl)ethylamines and C-(d-glycofuranosyl)methylamines as potential glycosidase inhibitors
  作者：Adel A.-H Abdel-Rahman、El Sayed H El Ashry、Richard R Schmidt

  DOI：10.1016/s0008-6215(98)00313-9

  日期：1999.1

  followed by catalytic hydrogenation and deprotection, gave the corresponding 1- C -(α- d -arabinofuranosyl)methylamine. Reductive amination of ethyl 2,3- O -isopropylidene-α- d - lyxo -pentodialdo-1,4-furanoside using aniline gave ethyl 5-anilino-5-deoxy- d - lyxo -furanoside. Inhibition studies with these compounds on β- d -glucosidase from sweet almond, using o -nitrophenyl d -glucopyranoside as substrate

  摘要由C-葡吡喃糖基丙烯前体经臭氧分解制备了C-葡糖醛，2-C-（2,3,4,6-四-O-乙酰基-α-d-吡喃吡喃糖基）乙醛。C-葡萄糖基醛的还原胺化和随后的脱保护得到1-苯胺基-2-C-（α-d-吡喃葡萄糖基）乙烷。通过用羟胺处理其醛前体来制备肟衍生物1-C-（α-d-阿拉伯呋喃糖基）甲氧基肟的E和Z异构体。肟的乙酰化，然后催化氢化和脱保护，得到相应的1-C-（α-d-阿拉伯呋喃糖基）甲胺。用苯胺将2，3-O-异亚丙基-α-d-lyxo-戊二醛-1，4-呋喃糖苷还原胺化，得到5-苯胺基-5-脱氧-d-lyxo-呋喃糖苷乙基。这些化合物对甜杏仁中β-d-葡萄糖苷酶的抑制作用研究，
• GLUCOSE DERIVATIVES BOUND TO ARSENIC FOR USE IN THE TREATMENT OF TUMOUR
  申请人：SALVETTI Marco

  公开号：US20150038694A1

  公开（公告）日：2015-02-05

  A family of sugar-based molecules for therapeutic use, includes compounds with a structure having at least one sugar molecule with carrier function, bound to arsenic having active principle function, allowing the selective therapeutic treatment of tumoral pathologies and not, distinguished by a high cellular metabolism and, consequently, by a high glucose consumption. Based on the preferential glucose absorption according to the Warburg effect, the compounds are adapted to penetrate inside tumoral cells and not, distinguished by a high cellular metabolism, via the glucose molecule integrated in their structure, so as to determine the selective therapeutic treatment of the cells and, consequently, of the pathologies deriving therefrom, by the arsenic molecule chemically bound to above mentioned glucose molecule. Processes for the production of synthetic sugar-based compounds and extracted sugar-based compounds, produced from natural sources are also described.

  一种用于治疗的基于糖分子家族，包括具有至少一个带有载体功能的糖分子结构，与具有活性原理功能的砷相结合的化合物，允许选择性治疗肿瘤病理和不具有高细胞代谢率和因此高葡萄糖消耗率的病理的区别。基于Warburg效应的优先葡萄糖吸收，这些化合物适应于通过其结构中集成的葡萄糖分子穿透肿瘤细胞，而不是区别于高细胞代谢率的细胞，从而通过化学上结合在上述葡萄糖分子上的砷分子确定对细胞和因此导致的病理的选择性治疗。还描述了生产合成糖基化合物和从天然来源提取的糖基化合物的过程。
• A short and efficient synthesis of α-C-(1 → 3)-linked disaccharides containing deoxyhexopyranoses
  作者：Petr Štěpánek、Ondřej Vı́ch、Ladislav Kniežo、Hana Dvořáková、Pavel Vojtı́šek

  DOI：10.1016/j.tetasy.2004.01.023

  日期：2004.3

  Ozonolysis of peracetylated α-d-glucopyranosylprop-2-ene, followed by the reaction of the formed ozonide with (thiazol-2-yl)carbonylmethylenetriphenyl phosphorane, afforded substituted 1-oxa-1,3-butadiene, which by a hetero-Diels–Alder reaction with ethyl vinyl ether gave a 1:1 mixture of two diastereoisomeric dihydropyran derivatives. These, after replacement of the acetyl protecting groups by benzyl

  将过乙酰化的α-d-吡喃葡萄糖基丙-2-烯进行臭氧分解，然后使所形成的臭氧化物与（噻唑-2-基）羰基亚甲基三苯基膦烷反应，得到取代的1-oxa-1,3-丁二烯，其通过杂Diels –与乙基乙烯基醚的Alder反应得到两种非对映异构体二氢吡喃衍生物的1：1混合物。在用苄基取代乙酰保护基之后，将它们通过色谱分离，并将它们的噻唑取代基转化为醛基。随后的硼氢化产生α- C-（1→3）-连接的二糖，其中d-葡萄糖通过亚甲基桥与2,3-二脱氧-阿拉伯糖连接。-d-或l-构型的六吡喃糖。所获得的化合物的结构已经通过NMR光谱法和X射线晶体学分析确认。
• A Stereocontrolled Access to α-<i>C</i>-(1→3)-Linked DisaccharidesContaining 2-Deoxyhexopyranoses
  作者：Ladislav Kniežo、Petr Štěpánek、Hana Dvořáková、Pavel Vojtíšek

  DOI：10.1055/s-2003-39288

  日期：——

  A protected α-d-glucopyranosylacetaldehyde was converted by Wittig reaction with (thiazol-2-yl)carbonylmethylene­triphenyl phosphorane into the corresponding substituted 1-oxa-1,3-butadiene which by hetero-Diels-Alder reaction with ethyl vinyl ether afforded a mixture of two diastereoisomeric dihydropyran derivatives. These were separated by chromatography and the thiazol ring was transformed into an aldehyde group. Subsequent hydro­boration afforded α-C-(1→3)-linked disaccharides containing 2-deoxyhexopyranoses of d- or l-configuration.

  一种受保护的δ-d-吡喃葡萄糖基乙醛通过与（噻唑-2-基）羰基亚甲基三苯基磷烷的 Wittig 反应转化为相应的取代 1-氧杂-1,3-丁二烯，再通过与乙烯基乙醚的杂 Diels-Alder 反应得到两种非对映异构的二氢吡喃衍生物混合物。这些衍生物通过色谱法分离，噻唑环转化为醛基。随后进行氢硼化合，得到了含有 d 或 l 构型的 2-脱氧己吡喃糖的 δ-C-（1→3）连接二糖。
• Spin-labelled glycolipid analogues: d-glucose series
  作者：Jean M.J. Tronchet、Martina Zsély、Michel Geoffroy

  DOI：10.1016/0008-6215(95)00177-u

  日期：1995.10

  Neoglycolipids bearing a paramagnetic probe in their lipophilic aglycon have been prepared. All belong to the D-glucose series, both anomers for the glucoside representatives, respectively beta and alpha anomers in the S- and C-glucosyl series. Two different types of radical sites have been used, a relatively short-lived imino N-oxyl group for glucosides and a more stable N-acylamino N-oxyl moiety in the other cases. EPR spectra of these radical species afforded information on the conformation of the lipophilic chain in the vicinity of the paramagnetic probe.