O-[3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl]-N-carbobenzyloxy-L-serine methyl ester | 1607459-38-0

• 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: O-[3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl]-N-carbobenzyloxy-L-serine methyl ester
• CAS: 1607459-38-0
• 化学式: C₂₄H₃₁NO₁₂
• 分子量: 525.51
• InChiKey: CTUSLPWSHVLEBC-POHUPDAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  161.99
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  N-((benzyloxy)carbonyl)-O-((2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-3-iodotetrahydro-2H-pyran-2-yl)-L-serine 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 23.0h， 生成 O-[3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl]-N-carbobenzyloxy-L-serine methyl ester
  参考文献：
  名称：

  Hypervalent Iodine Mediated Synthesis of C-2 Deoxy Glycosides and Amino Acid Glycoconjugates

  摘要：

  A simple, efficient, and practical method for the synthesis of C-2 deoxy-2-iodo glycoconjugates in self-assembled structures was found using PhI(OCOR)(2). 2-Iodo glycoserinyl esters were intramolecularly converted into 2-iodo serinyl glycosides which upon dehalogenation gave C-2 deoxy amino acid glycoconjugates.

  DOI：

  10.1021/jo500465m

文献信息

• TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
  作者：Mei-Yuan Hsu、Yi-Pei Liu、Sarah Lam、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3762/bjoc.12.164

  日期：——

  The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.

  甘露糖醛酸盐的硫加成反应可以在无溶剂条件下高效地通过等物量的溴化三甲基硅(TMSBr)催化产生良好至优异收率的S-2-脱氧糖苷。此外，加入三苯基膦氧化物作为添加剂，TMSBr介导的甘露糖醛酸盐与多种醇类的直接糖基化反应具有高度α-选择性。