(2R,3S,4S,5R,6R)-4-Allyloxy-2-ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,5-diol | 319921-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6R)-4-Allyloxy-2-ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,5-diol
• 英文别名: (2R,3S,4S,5R,6R)-2-ethylsulfanyl-6-(hydroxymethyl)-4-prop-2-enoxyoxane-3,5-diol
• CAS: 319921-96-5
• 化学式: C₁₁H₂₀O₅S
• 分子量: 264.343
• InChiKey: MHUPYOXKBBWZJE-SAVGLBRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-4-Allyloxy-2-ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,5-diol 在 sodium hydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-6-ethanesulfinyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Can preferential β-mannopyranoside formation with 4,6-O-benzylidene protected mannopyranosyl sulfoxides be reached with trichloroacetimidates?

  摘要：

  Studies with 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-alpha -D-mannopyranosyl sulfoxide (3d) and the corresponding trichloroacetimidate (4) as glycosyl donors and various accepters (A-F) led under similar reaction conditions to similar glycosylation results, i.e. mainly or exclusively the p-anomers of glycosides 5dA-5dF could be obtained. Thus, the versatile building block 5dA for N-glycan synthesis is readily available. For the activation of the sulfoxide leaving group, one equivalent of Tf2O and two equivalents of DTBMP are required, whereas for trichloroacetimidate activation catalytic amounts of TMSOTf are sufficient; hence, the trichloroacetimidate based procedure is very convenient. Various parameters were modified in the reaction of 4 with A (catalyst concentration, configuration of 4, size of the 2-O-protective group, solvent), thus, a proposal for the reaction course was derived. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01497-0
• 作为产物：
  描述：

  1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 三氟化硼乙醚 、 sodium methylate 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2R,3S,4S,5R,6R)-4-Allyloxy-2-ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,5-diol
  参考文献：
  名称：

  Can preferential β-mannopyranoside formation with 4,6-O-benzylidene protected mannopyranosyl sulfoxides be reached with trichloroacetimidates?

  摘要：

  Studies with 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-alpha -D-mannopyranosyl sulfoxide (3d) and the corresponding trichloroacetimidate (4) as glycosyl donors and various accepters (A-F) led under similar reaction conditions to similar glycosylation results, i.e. mainly or exclusively the p-anomers of glycosides 5dA-5dF could be obtained. Thus, the versatile building block 5dA for N-glycan synthesis is readily available. For the activation of the sulfoxide leaving group, one equivalent of Tf2O and two equivalents of DTBMP are required, whereas for trichloroacetimidate activation catalytic amounts of TMSOTf are sufficient; hence, the trichloroacetimidate based procedure is very convenient. Various parameters were modified in the reaction of 4 with A (catalyst concentration, configuration of 4, size of the 2-O-protective group, solvent), thus, a proposal for the reaction course was derived. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01497-0