ethyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside | 23345-65-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: ethyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6S)-3,5-diacetyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 23345-65-5
• 化学式: C₁₄H₂₀O₈
• 分子量: 316.308
• InChiKey: GBRDFTBUOLTNFG-YUTCNCBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Acetic acid (2R,3S,6S)-5-acetoxy-2-acetoxymethyl-6-hydroxy-3,6-dihydro-2H-pyran-3-yl ester 在 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 、 sodium cyanoborohydride 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 8.5h， 生成 ethyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Moufid, Nadira; Chapleur, Yves; Mayon, Patrick, Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 991 - 998

  摘要：

  DOI：

文献信息

• The reaction of 2-hydroxyglycal esters with alcohols in the presence of N-iodosuccinimide, stereoselective synthesis of α anomers of alkyl 3-deoxyhex-2-enopyranosides and 3,4-dideoxyhex-3-enopyranosid-2-uloses
  作者：Oscar Varela、Griselda M. de Fina、Rosa M. de Lederkremer

  DOI：10.1016/0008-6215(87)80278-1

  日期：1987.9

  Abstract Reaction of 2,3,4,6-tetra-O-acetyl-1,5-anhydro- d -arabino-hex-1-enitol (1; 2-hydroxyglucal tetraacetate) with 1.0–1.5 mol of primary secondary, or tertiary alcohols, in the presence of 0.1–1.0 mol of N-iodosuccinimide (NIS) in acetonitrile as solvent, afforded the α anomers of alkyl 3-deoxyhex-2-enopyranosides in very good yields. The reaction proceeded more slowly, and with poorer yields

  摘要2,3,4,6-四-O-乙酰基-1,5-脱水-阿拉伯-己糖-1-烯醇（1; 2-羟基葡糖四乙酸酯）与1.0-1.5 mol伯仲，或叔醇在乙腈中存在0.1–1.0 mol N-碘丁二酰亚胺（NIS）作为溶剂时，可以非常好的收率得到烷基3-deoxyhex-2-enopyranosides的α端基异构体。在四苯甲酸酯对应于1的情况下，反应进行得较慢，且收率较差。当1用较高浓度的2-丙醇处理时，反应副产物2-丙基6-O-乙酰基的比例增加产生了-3，4-二脱氧-α-d-甘油-己基-3-烯吡喃糖基-2-ulose（10）。当起始2-羟基乙酸乙酸酯具有lyxo构型时，更容易形成10这样的糖烯酮。因此，一步法制备了两种胆固醇基的α-hex-3-enopyranosid-2-ulose衍生物，并具有良好的收率。在所有这些反应中都观察到了形成α端基异构体的显着立体选择性。
• HClO4·SiO2 catalysed synthesis of alkyl 3-deoxy-hex-2-enopyranosides from 2-hydroxy glucal ester: application in the synthesis of a cis-fused bicyclic ether and a 4-amino-C-glucoside
  作者：Preeti Gupta、Nitee Kumari、Aditi Agarwal、Yashwant D. Vankar

  DOI：10.1039/b810654a

  日期：——

  A variety of alcohols react with 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabino-hex-1-enopyranose 1 in the presence of a catalytic amount of HClO4 supported on silica gel to give the corresponding alkyl 3-deoxy-hex-2-enopyranosides 2 in high yield, with short reaction times (10–45 mins) and good α-selectivity. Work-up merely involves filtration of the reagent, followed by chromatographic purification of the crude product. This methodology has also been employed in the synthesis of a bicyclic ether, a useful precursor for cyclic polyethers, and a 4-amino-C-glucoside.

  在硅胶负载的催化量高氯酸（HClO4）存在下，多种醇与2,3,4,6-四-O-乙酰基-1,5-脱水-D-阿拉伯型己-1-烯呋喃糖1反应，高效地生成相应的烷基3-脱氧-己-2-烯呋喃糖苷2，反应时间短（10–45分钟）且α-选择性良好。后处理仅涉及过滤试剂，随后对粗产品进行色谱纯化。这种方法也被应用于合成双环醚（环状聚醚的有用前体）和4-氨基-C-葡糖苷。
• Synthesis of a marine polyether toxin, okadaic acid (3) — synthesis of segment c
  作者：Yoshiyasu Ichikawa、Minoru Isobe、Hisanori Masaki、Takatoshi Kawai、Toshio Goto

  DOI：10.1016/s0040-4020(01)86917-9

  日期：1987.1

  The title compound was divided into three retrosynthetic segments, A, B and C, by disconnecting two C-C bonds at C- and C-. Synthesis of the segment C in the optically active natural form starting from a D-glucose derivatives is described. The key features are stereochemical control which includes a methodology named heteroconjugate addition involving carbon chain extension using carbanion stabilized

  标题化合物，分为三个逆合成片段，A，B和C，通过断开在C- 2个CC键和C- 。描述了以D-葡萄糖衍生物为原料的旋光天然形式的链段C的合成。关键特征是立体化学控制，其中包括一种名为杂共轭加成的方法，该方法涉及使用通过苯基磺酰基稳定的碳负离子进行碳链延伸。