methyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside | 220051-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside
• 英文别名: (3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-6-[(2R)-oxiran-2-yl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 220051-10-5
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: IDKNYMXZGDICCP-DFTQBPQZSA-N

物化性质

• 沸点：
  280.9±40.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 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：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside 在 potassium tert-butylate 、 sodium acetate 作用下， 反应 0.5h， 生成 Acetic acid (R)-3-acetoxy-1-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propyl ester
  参考文献：
  名称：

  Synthesis of 6-Deoxyheptose Derivatives via Cyclic Sulfates and Oxetanes

  摘要：

  DOI：

  10.1055/s-1998-2219
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-α-D-mannofuranoside 在 吡啶 、 sodium methylate 、 2-萘磺酰氯 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 26.0h， 生成 methyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside
  参考文献：
  名称：

  Synthesis of 6-Deoxyheptose Derivatives via Cyclic Sulfates and Oxetanes

  摘要：

  DOI：

  10.1055/s-1998-2219

文献信息

• [EN] SYNTHESIS OF 10-alpha/beta-D-ARABINOFURANOSYL-UNDECENES AS POTENTIAL ANTI-MYCOBACTERIAL AGENTS<br/>[FR] SYNTHÈSE DE 10 D-ARABINOFURANOSYL-UNDÉCÈNES POTENTIELLEMENT UTILES COMME AGENTS ANTI-MYCOBACTÉRIENS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2013038430A1

  公开（公告）日：2013-03-21

  Disclosed herein is 10-α/β-D-Arabinofuranosylundecenes of general Formula (II) or pharmaceutically acceptable salts thereof as anti-mycobacterial agents in vitro; (II) wherein R, R1 and R" are as defined herein in the specification. The present invention also discloses a simple stereoselective synthesis 10-α/β-D-Arabinofuranosylundecenes of Formula (II) to target enzymes involved in the biosynthesis of cell wall of Mycobacterium and thus useful as inhibitors in the Mycobacterium tuberculosis drug development.

  本文公开了一种通用公式（II）的10-α/β-D-阿拉伯呋喃糖基十一烯或其药用盐，作为体外抗分枝杆菌药物；（II）其中R、R1和R"如本说明书中所定义。本发明还公开了一种简单的立体选择性合成10-α/β-D-阿拉伯呋喃糖基十一烯的方法，以靶向参与结核分枝杆菌细胞壁生物合成的酶，并因此在结核分枝杆菌药物开发中作为抑制剂有用。
• Stereospecific synthesis of C-arabinofuranosides and carba-disaccharide analogues of Motif C of cell wall AG complex of Mtb
  作者：Rahul S. Patil、Ketan M. Ahire、C.V. Ramana

  DOI：10.1016/j.tetlet.2012.09.015

  日期：2012.11

  A simple strategy for the synthesis of alpha- and beta-C-arabinofuranosides featuring a furan ring transposition reaction has been developed. A novel double furan ring transposition reaction has proposed and executed for the synthesis of the carba-disaccharide analogue of Motif C of the cell wall AG complex of Mtb. (C) 2012 Elsevier Ltd. All rights reserved.
• A new 6-C-alkylation from an alkyl mannofuranoside 5,6-cyclic sulfate
  作者：Thierry Gourlain、Anne Wadouachi、Daniel Beaupère

  DOI：10.1016/s0008-6215(99)00275-x

  日期：2000.1

  Methyl 6-C-alkyl-6-deoxy-alpha-D-mannofuranoside derivatives have been synthesized from methyl 2,3-O-isopropylidene-5,6-O-sulfuryl-alpha-D-mannofuranoside (1). In a Path A, reaction of the 5,6-cyclic sulfate 1 with 2-lithio-1,3-dithiane afforded 2-(methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-mannofuranosid-6-yl)-1,3-dithiane (2). Treatment of 2 with n-butyllithium then alkyl iodide gave the corresponding 2-(methyl 5-O-alkyl-6-deoxy-2,3-O-isopropylidene-alpha-D-mannofuranosid-6-yl)-1,3-dithiane. Reaction of 2 with n-butyllithium and 5,6-cyclic sulfate 1 furnished 2-[methyl 6-deoxy-2,3-O-isopropylidene-5-O-(methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-manno-furanosid-6-yl)-alpha-D-mannofuranosid-6-yl]-1,3-dithiane. 2-(Methyl 6-deoxy-2,3-O-isopropylidene-5-O-methyl-alpha-D-mannofuranosid-6-yl)-1,3-dithiane was converted into the lithiated anion, which after treatment with alkyl halide afforded the corresponding 2-alkyl-C-(methyl 6-deoxy-2,3-O-isopropylidene-5-O-methyl-alpha-D-mannofuranosid-6-yl)-1,3-dithiane. In a Path B, 5,6-cyclic sulfate 1 reacted with 2-alkyl-2-lithio-1,3-dithiane derivatives, which led after acidic hydrolysis to 2-alkyl-2-(methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-mannofuranosid-6-yl)-1,3-dithiane accompanied by methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranos-5-uloside as the by-product. This methodology was applied to synthesize 2-(methyl 6-deoxy-2,3-O-isopropylidene-5-O-methyl-alpha-D-mannofuranosid-6-yl)-2-(methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-mannofuranosid-6-yl)-1,3-dithiane. (C) 2000 Elsevier Science Ltd. All rights reserved.
• ——
  作者：Tadashi Hanaya、Hiroshi Yamamoto

  DOI：10.1002/1522-2675(200209)85:9<2608::aid-hlca2608>3.0.co;2-f

  日期：2002.9

  Starting from methyl 2,3-O-isopropylidene-alpha-D-mannofuranoside (5), methyl 6-O-benzyl-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose (12) was prepared in three steps. The addition reaction of dimethyl phosphonate to 12, followed by deoxygenation of 5-OH group, provided the 5-deoxy-5-dimetltoxyphosphinyl-alpha-D-mannofuranoside derivative 15a and the beta-L-gulofuranoside isomer 15b. Reduction of 15a and 15b with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of HCl and then H2O2, afforded the D-mannopyranose (17) and L-gulopyranose analog 21, each having a phosphinyl group in the hemiacetal ring. These were converted to the corresponding 1,2,3,4,6-penta-O-acetyl-5-methoxyphosphinyl derivatives 19 and 23, respectively, structures and conformations (C-4(1) or C-1(4), resp.) of which were established by H-1-NMR spectroscopy.
• Synthesis of 6-Deoxyheptose Derivatives via Cyclic Sulfates and Oxetanes
  作者：Antonio Vargas-Berenguel、Francisco Santoyo-González、José A. Calvo-Asín、Francisco G. Calvo-Flores、Juan M. Expósito-López、Fernando Hernández-Mateo、Joaquín Isac-García、Juan J. Giménez Martínez

  DOI：10.1055/s-1998-2219

  日期：1998.12