3,6-anhydro-1,2:4,5-di-O-isopropylidene-D-glycero-D-manno-heptitol | 144651-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-anhydro-1,2:4,5-di-O-isopropylidene-D-glycero-D-manno-heptitol
• 英文别名: 3,6-anhydro-1,2,4,5-di-O-isopropylidene-D-glycero-D-mannoheptitol；2,5-anhydro-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptitol；[(3aS,4R,6R,6aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 144651-34-3；144732-47-8
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: RQJXVTDIPBQDFO-ILAIQSSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-anhydro-1,2:4,5-di-O-isopropylidene-D-glycero-D-manno-heptitol 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 2,5-anhydro-3,4:6,7-di-O-isopropylidene aldehydo-D-glycero-D-galacto-heptofuranose
  参考文献：
  名称：

  Tetra-n-butylammonium fluoride: an efficient base for aza-Michael addition—synthesis of glycosyl β-amino acid esters

  摘要：

  A mild and efficient route to glycosyl beta-amino acid esters. exploiting the stereoselective Michael addition of benzylamine, in the presence of tetra-n-butylammonium fluoride, to sugar derived gamma-alkoxy alpha,beta-unsaturated esters is described. (C) 2602 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00047-2
• 作为产物：
  描述：

  D-甘露糖 在 硫酸 、 potassium tert-butylate 、 copper(II) sulfate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.5h， 生成 3,6-anhydro-1,2:4,5-di-O-isopropylidene-D-glycero-D-manno-heptitol
  参考文献：
  名称：

  Synthesis of N-homobicyclic dideoxynucleoside analogues

  摘要：

  Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by fractional crystallization. The two stereoisomers were converted to bicyclic furanolactols each of which was coupled with three nucleoside bases. Further debenzylations gave the six target N-homobicyclic dideoxynucleosides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.018

文献信息

• Intramolecular Hydrogen Abstraction Reaction Promoted by Alkoxy Radicals in Carbohydrates. Synthesis of Chiral 2,7-Dioxabicyclo[2.2.1]heptane and 6,8-Dioxabicyclo[3.2.1]octane Ring Systems
  作者：Cosme G. Francisco、Antonio J. Herrera、Ernesto Suárez

  DOI：10.1021/jo026004z

  日期：2002.10.1

  for the synthesis of chiral 6,8-dioxabicyclo[3.2.1]octane and 2,7-dioxabicyclo[2.2.1]heptane ring systems under neutral conditions. This reaction can be considered to be an intramolecular glycosidation that goes through an intramolecular hydrogen abstraction promoted by an alkoxy radical followed by oxidation of the transient C-radical intermediate to an oxycarbenium ion. This methodology is useful

  特定保护的脱水醛糖醇与（二乙酰氧基碘）苯或碘基苯与碘的反应是合成手性6,8-二氧杂双环[3.2.1]辛烷和2,7-二氧杂双环[2.2.1]庚烷环的温和选择性步骤系统在中性条件下。该反应可被认为是分子内糖苷化，其经历由烷氧基自由基促进的分子内氢提取，然后将瞬时的C-自由基中间体氧化成氧碳鎓离子。该方法不仅可用于手性合成子的制备，而且可用于碳水化合物骨架的特定碳的选择性氧化，这是合成被保护的果糖的良好方法。
• Synthesis and conformational studies of peptides from new C-linked carbo-β-amino acids (β-Caas) with anomeric methylamino- and difluorophenyl moieties
  作者：Gangavaram V. M. Sharma、Velaparthi Subash、Nelli Yella Reddy、Kongari Narsimulu、Rapolu Ravi、Vivekanand B. Jadhav、Upadhyayula S. N. Murthy、Kankipati Hara Kishore、Ajit C. Kunwar

  DOI：10.1039/b810817j

  日期：——

  New C-linked carbo-β-amino acids (β-Caas), Cbz-(S)-β-Caa-(NHBoc)-OMe (1) and Cbz-(R)-β-Caa-(NHBoc)-OMe (2), with an additional amine group (methylamino group of NHBoc) at the C-1 position of the lyxofuranoside side chain and Boc-(S)-β-Caa-(diFP)-OMe (3) and Boc-(R)-β-Caa-(diFP)-OMe (4), with a C-difluorophenyl (diFP) moiety at the anomeric position of the lyxofuranoside side chain were prepared from D-mannose. β-Peptides [tetra- and hexapeptides] were synthesized from these β-Caas, ‘epimeric’ [at the amine stereocentre (Cβ)], using the concept of ‘alternating chirality’ to carry out their conformational studies [NMR (CDCl3), CD and MD]. In the monomer design, it was envisaged that the presence of an additional amine group in 1 or 2 would help in solubilizing the peptides in water, while, the C-difluorophenyl (diFP) moiety of 3 and 4 is expected to enhance the biological activity. The peptides having 1 and 2, though could not retain their 12–10-mixed helices in water, have shown moderate activity against Gram positive and Gram negative bacterial strains. The peptides prepared from 3 and 4, much against our expectations, did not display any biological activity.

  新的 C 连接碳-β-氨基酸 (β-Caas)、Cbz-(S)-β-Caa-(NHBoc)-OMe (1) 和 Cbz-(R)-β-Caa-(NHBoc)-OMe (2)，在 lyxofuranoside 侧链的 C-1 位置上有一个额外的胺基团（NHBoc 的甲基氨基）和 Boc-(S)-β-Caa-(diFP)-OMe (3) 和 Boc-(R )-β-Caa-(diFP)-OMe (4)，在lyxofuranoside 侧链的异头位置具有C-二氟苯基(diFP) 部分，由D-甘露糖制备。 β-肽[四肽和六肽]是从这些β-Caas、“差向异构体”[在胺立构中心(Cβ)]合成的，使用“交替手性”的概念来进行构象研究[NMR (CDCl3)、CD 和 MD]。在单体设计中，预计1或2中额外胺基的存在将有助于将肽溶解在水中，而3和4中的C-二氟苯基（diFP）部分预计将增强生物活性。具有1和2的肽虽然不能在水中保留其12-10混合螺旋，但已显示出针对革兰氏阳性和革兰氏阴性细菌菌株的中等活性。由3和4制备的肽，与我们的预期非常不同，没有表现出任何生物活性。
• Stereoselective synthesis of (2R,3S,4S,5R)-trans-3,4-dihydroxy-5-(4-fluorophenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)tetrahydrofuran and (2R,3S,4S,5R)-trans-5-ethynyl-2-(4-fluorophenoxymethyl)-3,4-O-isopropylidene tetrahydrofuran from mannose diacetonide
  作者：G.V.M. Sharma、Sreenivas Punna、Lanka Hymavathi、N. Yella Reddy、Palakodety Radha Krishna、Mukund S. Chorghade、Steven V. Ley

  DOI：10.1016/j.tetasy.2005.01.046

  日期：2005.3

  Stereoselective synthesis of pharmaceutically interesting chiral tetrahydrofurans starting from mannose diacetonide is reported. A 1,4-diol system derived from mannose diacetonide, through a Mitsunobu reaction was stereo specifically cyclized to give chiral tetrahydrofurans. Both the C-1 and C-4 centers Of D-mannose are successfully exploited to install the requisite side chains. (C) 2005 Elsevier Ltd. All rights reserved.
• Inhibition of α-mannosidases by seven carbon sugars: Synthesis of some seven carbon analogues of mannofuranose
  作者：Paul M. Myerscough、Antony J. Fairbanks、Aled H. Jones、Ian Bruce、Sik-man S. Choi、George W.J. Fleet、Samer S. Al-Daher、Isabelle Cenci di Bello、Bryan Winchester

  DOI：10.1016/s0040-4020(01)89046-3

  日期：——

  The effects on human liver glycosidases of some seven carbon analogues of mannopyranose and mannofuranose are compared with those of deoxymannojirimycin and DIM. The syntheses of the seven carbon mannofuranose analogues, alpha-(aminomethyl)-1-deoxy-mannofuranose and of alpha-homoDIM, are described.
• Réaction d'Ylures du soufre sur des sucres réducteurs: Application à la synthèse d'hydroxyméthyl C-glycosides.
  作者：C. Fréchou、L. Dheilly、D. Beaupère、R. Uzan、G. Demailly

  DOI：10.1016/s0040-4039(00)61191-7

  日期：1992.8

  Treatment of reducing carbohydrates with unstabilized sulfur ylides affords epoxy alcohols. When the reaction is not accompanied by elimination of a leaving group at C-3, spontaneous cyclisation occurs, and hydroxymethyl C-glycosyl compounds are obtained.