2,5-anhydro-3,4,6-tri-O-benzyl-D-altrohexofuranose | 160701-96-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-3,4,6-tri-O-benzyl-D-altrohexofuranose
• 英文别名: (2S,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane-2-carbaldehyde
• CAS: 160701-96-2
• 化学式: C₂₇H₂₈O₅
• 分子量: 432.516
• InChiKey: FHNGZJPNWWCNKW-JVYGEBFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,4,6-tri-O-benzyl-D-altrohexofuranose 在 二乙胺 、 异丙醇 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 甲醇 、 乙醚 为溶剂， 反应 24.17h， 生成 (2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl alcohol
  参考文献：
  名称：

  SmI 2诱导的噻唑基酮糖的脱氧对甲酰基C-糖苷合成的选择性和C-核呋喃糖苷的修饰结构

  摘要：

  使用SmI 2-（CH 2 OH）2或TMSOTf-Et 3 SiH对乙酸噻唑基酮糖乙酸进行脱氧，得到具有相反α/β比的噻唑基C-糖苷。通过NOE实验对噻唑基α-和β- C-核呋喃糖苷对的研究表明，必须修改分配给这些异构体之一的早期构型。已经制备正品异头α-和β-D-呋喃核糖醛从相应的噻唑基C ^由噻唑环的裂解-glycosides，各醛转化到（1→6） - c ^通过Wittig烯化-disaccharides与半乳糖6-正膦。

  DOI：

  10.1016/s0040-4020(01)00736-0
• 作为产物：
  描述：

  2-((2S,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-thiazolidine 在 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 生成 2,5-anhydro-3,4,6-tri-O-benzyl-D-altrohexofuranose
  参考文献：
  名称：

  SmI 2诱导的噻唑基酮糖的脱氧对甲酰基C-糖苷合成的选择性和C-核呋喃糖苷的修饰结构

  摘要：

  使用SmI 2-（CH 2 OH）2或TMSOTf-Et 3 SiH对乙酸噻唑基酮糖乙酸进行脱氧，得到具有相反α/β比的噻唑基C-糖苷。通过NOE实验对噻唑基α-和β- C-核呋喃糖苷对的研究表明，必须修改分配给这些异构体之一的早期构型。已经制备正品异头α-和β-D-呋喃核糖醛从相应的噻唑基C ^由噻唑环的裂解-glycosides，各醛转化到（1→6） - c ^通过Wittig烯化-disaccharides与半乳糖6-正膦。

  DOI：

  10.1016/s0040-4020(01)00736-0

文献信息

• Thiazole-Based Synthesis of Formyl C-Glycosides
  作者：Alessandro Dondoni、Marie-Christine Scherrmann

  DOI：10.1021/jo00100a050

  日期：1994.10

  A method for the installation of the formyl group at the anomeric position of pyranoses and furanoses starting from the corresponding lactones has been developed. The strategy involves the addition of 2-lithiothiazole to the sugar lactone, followed by the silane reduction of the acetylated resultant ketol and the unmasking of the formyl group from the thiazole ring. All steps have been studied in some details to improve chemical efficiency and stereochemical control. Hence, reversed alpha:beta ratios of ketols were found in kinetic and thermodynamic mixtures, the former being consistent with a steric effect control of the substituents and the latter by the electronic effect of the ring oxygen. Seven sugar aldehydes with different D-pyranosidic (2,3,4,6-tetra-O-benzyl-gluco, -galacto, and -manno, 2-azido-3,4,6-tri-O-benzyl-2-deoxy-galacto) and D-furanosidic moieties (5-O-benzyl-2,3-isopropylidene-ribo; 2,3,5-tri-O-benzyl-ribo; 2,3:5,6-di-O-isopropylidene-manno) were prepared in 52-65% isolated overall yield from the corresponding lactone.
• Synthesis of α- and β-<scp>d</scp>-(1→6)-<i>C</i>-Disaccharides by Wittig Olefination of Formyl <i>C</i>-Glycosides with Glycopyranose 6-Phosphoranes
  作者：Alessandro Dondoni、Helene M. Zuurmond、Alessia Boscarato

  DOI：10.1021/jo971177n

  日期：1997.11.1

  The synthesis of (1-->6)-C-disaccharides by Wittig condensation of formyl C-glycofuranosides and pyranosides with galacto-and glucopyranose B-phosphoranes is described herein. The method involves the coupling of the sugar aldehydes with the ylides and the reduction of the double bond of the resulting sugar alkenes, in most of the cases by catalytic hydrogenation. The reduction with nickel boride or diimide is employed in some special cases. O-Benzyl protective groups are removed by catalytic hydrogenation either in the course of the reduction of the double bond or in a subsequent step, while O-isopropylidene groups are cleaved by treatment with Amberlite IR-120. In this way, eight free beta-D-(1-->6)-C-disaccharides have been prepared in 26-61% overall yield starting from B-linked formyl C-glycosides. These include C-linked analogues of the biologically active disaccharides allolactose (Gal beta 1,6Glc), gentiobiose (Glc beta 1,6Glc), and N-acetylamino disaccharides (GalNHAc beta,6Gal and GalNHAc beta 1,6Glc). Moreover, the synthesis of two alpha-D-(1-->6)-C-disaccharides is described from formyl C-furanosides. The limiting condition of the synthesis of these stereoisomers is the configurational instability of the alpha-linked formyl C-glycosides under the basic conditions of the Wittig olefination.
• Selectivity in the SmI2-induced deoxygenation of thiazolylketoses for formyl C-glycoside synthesis and revised structure of C-ribofuranosides
  作者：Alessandro Dondoni、Paolo Formaglio、Alberto Marra、Alessandro Massi

  DOI：10.1016/s0040-4020(01)00736-0

  日期：2001.9

  Deoxygenation of thiazolylketose acetates using SmI2–(CH2OH)2 or TMSOTf–Et3SiH affords thiazolyl C-glycosides with opposite α/β ratios. Examination of the thiazolyl α- and β-C-ribofuranoside pair by NOE experiments reveals that the earlier configuration assigned to one of these isomers has to be revised. Having prepared authentic anomeric α- and β-ribofuranose aldehydes from the corresponding thiazolyl

  使用SmI 2-（CH 2 OH）2或TMSOTf-Et 3 SiH对乙酸噻唑基酮糖乙酸进行脱氧，得到具有相反α/β比的噻唑基C-糖苷。通过NOE实验对噻唑基α-和β- C-核呋喃糖苷对的研究表明，必须修改分配给这些异构体之一的早期构型。已经制备正品异头α-和β-D-呋喃核糖醛从相应的噻唑基C ^由噻唑环的裂解-glycosides，各醛转化到（1→6） - c ^通过Wittig烯化-disaccharides与半乳糖6-正膦。