Ethyl 2,3,4,6-Tetra-O-benzyl-C-α-D-glucopyranoside | 116417-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 2,3,4,6-Tetra-O-benzyl-C-α-D-glucopyranoside
• 英文别名: (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-ethane α anomer；α-1,5-anhydro-1-C-ethyl-2,3,4,6-tetra-O-benzyl-D-glucitol；1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-ethane；(2R,3S,4R,5R,6R)-2-ethyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 116417-37-9
• 化学式: C₃₆H₄₀O₅
• 分子量: 552.711
• InChiKey: JQVBMLQFSYWPFV-SQGINLDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,3r,4s,5r,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃 、 三乙基铝 生成 Ethyl 2,3,4,6-Tetra-O-benzyl-C-α-D-glucopyranoside
  参考文献：
  名称：

  TOLSTIKOV, G. A.;PROXOROVA, N. A.;SPIVAK, A. YU., 5 BCEC. KONF. PO METALLOORGAN. XIMII, YURMALA, 1-4 APR., 1991: TEZ. DOKL.+

  摘要：

  DOI：

文献信息

• Organometallics in organic synthesis. Applications of a new diorganozinc reaction to the synthesis of C-glycosyl compounds with evidence for an oxonium-ion mechanism
  作者：Alan P. Kozikowski、Toshiro Konoke、Allen Ritter

  DOI：10.1016/s0008-6215(00)90882-6

  日期：1987.12

  features of a new organozinc-based substitution process [heteroatom-C-(R1,R2)-SPh + R3(2)Zn----heteroatom-C-(R1,R2,R3)], first discovered during a total synthesis of the alkaloid mycotoxin alpha-cyclopiazonic acid, are described. Phenyl thioglycosides were valuable substrates in studying the nature of this reaction process. Since these sulfur compounds are converted into C-glycosyl compounds with some

  首次发现新的基于有机锌的取代过程[杂原子-C-（R1，R2）-SPh + R3（2）Zn ----杂原子-C-（R1，R2，R3）]的机理和立体化学特征在生物碱真菌毒素的全合成过程中，描述了α-环吡嗪酸。苯基硫代糖苷是研究该反应过程性质的有价值的底物。由于这些硫化合物以一定的立体选择性转化为C-糖基化合物，因此有机锌化学确实为这些生物活性物质提供了新的进入途径。
• Application of Redox-Active Ester Catalysis to the Synthesis of Pyranose Alkyl <i>C</i>-Glycosides
  作者：Joseph R. Romeo、Jon D. Lucera、Drew Jensen、Luke M. Davis、Clay S. Bennett

  DOI：10.1021/acs.orglett.3c01228

  日期：2023.5.26

  The direct coupling of shelf-stable, tetrachloro-N-hydroxyphthalimide ester (TCNHPI) glycosyl donors with a variety of alkylzinc reagents under redox catalysis is described. Alkyl C-glycosides are formed directly by a decarboxylative, Negishi-type process in 31–73% yields without the need for photocatalytic activation or additional reductants. Extension of this approach to the coupling of TCNHPI donors

  描述了货架稳定的四氯-N-羟基邻苯二甲酰亚胺酯 (TCNHPI) 糖基供体与各种烷基锌试剂在氧化还原催化下的直接偶联。烷基C-糖苷通过脱羧、Negishi 型工艺直接形成，产率为 31-73%，无需光催化活化或额外的还原剂。将这种方法扩展到 TCNHPI 供体与立体定义的含 α-烷氧基呋喃的烷基卤化锌的偶联，能够通过 Achmatowicz 重排从头合成亚甲基连接的外型-C-二糖。
• Tolstikov, G. A.; Prokhorova, N. A.; Spivak, A. Yu., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 10, p. 1858 - 1863
  作者：Tolstikov, G. A.、Prokhorova, N. A.、Spivak, A. Yu.、Khalilov, L. M.、Sultanmuratova, V. R.

  DOI：——

  日期：——
• TOLSTIKOV, G. A.;PROXOROVA, N. A.;SPIVAK, A. YU., 5 BCEC. KONF. PO METALLOORGAN. XIMII, YURMALA, 1-4 APR., 1991: TEZ. DOKL.+
  作者：TOLSTIKOV, G. A.、PROXOROVA, N. A.、SPIVAK, A. YU.

  DOI：——

  日期：——