1,6-anhydro-4-deoxy-2-O-p-toluenesulphonyl-β-D-xylo-hexopyranose | 23643-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-4-deoxy-2-O-p-toluenesulphonyl-β-D-xylo-hexopyranose
• 英文别名: 1,6-anhydro-4-deoxy-2-O-p-toluenesulfonyl-β-D-xylo-hexopyranose；1,6-anhydro-4-deoxy-2-O-p-toluenesulphonyl-β-D-glucopyranose；1,6-Anhydro-4-deoxy-2-O-tosyl-β-D-xylo-hexopyranose；1,6-anhydro-4-deoxy-2-O-tosyl-β-D-xylohexopyranose；1,6-anhydro-4-deoxy-2-O-tosyl-β-D-xylopyranose；2-O-Tosyl-1,6-anhydro-4-desoxy-β-D-xylohexopyranose；[(1S,3S,4R,5R)-3-hydroxy-6,8-dioxabicyclo[3.2.1]octan-4-yl] 4-methylbenzenesulfonate
• CAS: 23643-30-3
• 化学式: C₁₃H₁₆O₆S
• 分子量: 300.332
• InChiKey: YEBYJAHNNHNJDH-FTYKPCCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-4-deoxy-2-O-p-toluenesulphonyl-β-D-xylo-hexopyranose 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 sodium hydride 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.5h， 生成 (1RS,2S,3S,5S)-2-Acetamido-2,4-dideoxyhexopyranose
  参考文献：
  名称：

  Cerny, Ivan; Trnka, Tomas; Cerny, Miloslav, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 8, p. 2386 - 2394

  摘要：

  DOI：
• 作为产物：
  描述：

  1,6:3,4-二脱水-2-O-对甲苯磺酰基-beta-D-吡喃半乳糖 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 乙二醇二甲醚 为溶剂， 反应 21.0h， 以92%的产率得到1,6-anhydro-4-deoxy-2-O-p-toluenesulphonyl-β-D-xylo-hexopyranose
  参考文献：
  名称：

  Two Unusual Carbohydrate Reactions: Nucleophilic Ring Opening of an Anhydrosugar and Reductive Elimination with Co‐occurring Hydrogenation

  摘要：

  Treatment of the 1,6-anhydrosugar epoxide 5 with a cyano-Gilman cuprate [(CuCN (6 eq.), MeLi (12 eq.)] surprisingly led to the open chain rearranged (2S,3R)-1,2-dihydroxy-3,6-dimethylheptan-4-one (7), structurally confirmed by conversion to the corresponding diacetate 8. Another unusual reaction was found by hydrogenation of the 2-tosyl-1-bromosugar 11, leading in one operation to the twofold deoxygenated chiral pyran derivative 14. This procedure might prove to be useful in the rapid deoxygenation of sugar derivatives.

  DOI：

  10.1080/07328300802272389

文献信息

• Carbamates : A method of synthesis and some syntehtic applications
  作者：Pavel Kočovský

  DOI：10.1016/s0040-4039(00)85256-9

  日期：1986.1

  Alcohols are converted into unsubstituted carbamates by treatment with trichloroacetyl isocyanate followed by hydrolysis on Al2O3. This extremely mild procedure tolerates various labile functional groups. The synthetic utility of the carbamate moiety as a control element is demonstrated on epoxidation and epoxide opening.

  通过用三氯乙酰基异氰酸酯处理，然后在Al 2 O 3上水解，将醇转化为未取代的氨基甲酸酯。这种极其温和的程序可以耐受各种不稳定的功能基团。氨基甲酸酯部分作为控制元素的合成效用在环氧化和环氧化物开环中得到证明。
• Synthesis of Unsaturated Sulfur-Linked (1→4)-Disaccharides by Substitution of Tosyloxy Group in 1,6-Anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose with 1-Thiohexopyranoses
  作者：Petr Bartoš、Miloslav Černý、Iva Tišlerová、Tomáš Trnka

  DOI：10.1135/cccc20001737

  日期：——

  A novel method for the synthesis of unsaturated sulfur-linked (1→4)-disaccharides is described. The starting 1,6-anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose (3) was reacted with potassium salt of acetylated 1-thiohexopyranoses of D-gluco-, D-galacto-, and L-galacto-configuration to give acetylated β-glycopyranosyl-(1→4)-1,6-anhydro-2,3-dideoxy-4-thio-β-D-erythro-hex-2-enopyranoses 8-10. Their acid methanolysis under mild conditions afforded the corresponding methyl glycosides 11-13. The structure of new compounds was confirmed by ¹H NMR and mass spectra data.

  描述了一种合成不饱和硫连接的（1→4）-二糖的新方法。起始物1,6-脱水-3,4-二脱氧-2-O-对甲苯磺酰-β-D-赤霉醇-3-烯吡喃糖（3）与D-葡萄糖、D-半乳糖和L-半乳糖构型的乙酰化1-硫代己糖吡喃糖的钾盐反应，得到了乙酰化的β-葡萄糖吡喃糖-(1→4)-1,6-脱水-2,3-二脱氧-4-硫-β-D-赤霉醇-2-烯吡喃糖（8-10）。它们在温和条件下进行酸甲醇解，得到相应的甲基糖苷（11-13）。新化合物的结构经过1H NMR和质谱数据确认。
• Schraml, Jan; Vcelak, Jaroslav; Cerny, Miloslav, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 9, p. 2503 - 2508
  作者：Schraml, Jan、Vcelak, Jaroslav、Cerny, Miloslav、Chvalovsky, Vaclav

  DOI：——

  日期：——
• Banaszek, Anna, Bulletin of the Polish Academy of Sciences: Chemistry, 1984, vol. 32, # 3-6, p. 99 - 104
  作者：Banaszek, Anna

  DOI：——

  日期：——
• Improved preparation of 1,6-anhydro-4-deoxy-2-O-p-toluenesulphonylβ-d-xylo-hexopyranose and of its d-[4-2H]gluco-analogue from 1,6 : 3,4-dianhydro-2-O-p-toluenesulphonyl-β-d-galactopyranose
  作者：Tomáš Trnka、Miloš Buděšínský、Miloslav Černý

  DOI：10.1016/0008-6215(94)84203-5

  日期：1994.6