α-methyl-6-O-(dihydroxyphosphoryl)-D-mannopyranoside | 15416-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-methyl-6-O-(dihydroxyphosphoryl)-D-mannopyranoside
• 英文别名: methyl α-D-mannopyranoside 6-phosphate；MeM6P；Methyl-α-D-mannopyranosid-6-phosphat；[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl dihydrogen phosphate
• CAS: 15416-98-5；33985-22-7；46826-29-3；92760-89-9；106189-46-2
• 化学式: C₇H₁₅O₉P
• 分子量: 274.164
• InChiKey: RXYNVAYAPLNZFK-VEIUFWFVSA-N

物化性质

• 沸点：
  537.3±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  甲基-D-丙噻 在 吡啶 、 4-二甲氨基吡啶 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到α-methyl-6-O-(dihydroxyphosphoryl)-D-mannopyranoside
  参考文献：
  名称：

  6-磷酸甘露糖类似物的合成及其作为血管生成调节剂的作用

  摘要：

  实用价值低：据报道，一种有效的方法使用关键的环状硫酸盐中间体合成了在C-6位置修饰的甘露糖-6-磷酸酯（M6P）类似物。这些类似物代表了第一个已知的血管生成单糖效应子。此外，此处报道的结果证实了M6P受体参与了血管形成。

  DOI：

  10.1002/cmdc.201100293

文献信息

• Control of Phosphoryl Migratory Transesterifications Allows Regioselecive Access to Sugar Phosphates
  作者：Mitul K. Patel、Benjamin G. Davis

  DOI：10.1021/ol303271z

  日期：2013.1.18

  Phosphate esters in polyhydroxylated systems are normally blighted by uncontrolled migration under a variety of reaction conditions. Cesium fluoride is demonstrated as a reagent to control migration of primary phosphates during transesterifications. This allows easy exchange of phosphoryl protecting groups enabling enhanced synthetic strategic flexibility and regioselective phosphate installation.

  多羟基化体系中的磷酸酯通常会在各种反应条件下因不受控制的迁移而受损。氟化铯被证明是一种试剂，可在酯交换过程中控制伯磷酸盐的迁移。这允许轻松交换磷酸保护基团，从而增强合成战略灵活性和区域选择性磷酸盐安装。机理分析表明，氟化物诱导的扩展溶剂球调节磷的空间体积以有利于主要位置。
• NOVEL USES OF D-MANNOPYRANOSE DERIVATIVES
  申请人：Monteron Jean-Louis

  公开号：US20110112044A1

  公开（公告）日：2011-05-12

  The invention relates to the use of mannose-6-phosphate (M6P) and of certain derivatives thereof for controlling angiogenesis and ligament regeneration and/or cartilage reconstruction. The MP6 and certain derivatives thereof can particularly be used for preparing a pharmaceutical composition used for ligament regeneration and/or cartilage reconstruction.

  该发明涉及利用甘露糖-6-磷酸（M6P）及其某些衍生物来控制血管生成、韧带再生和/或软骨重建。M6P及其某些衍生物特别可用于制备用于韧带再生和/或软骨重建的药物组合物。
• Synthesis, NMR, and conformational studies of methyl α-d-mannopyranoside 2-, 3-, 4-, and 6-monophosphates
  作者：Christian Bernlind、Stefan Oscarson、Göran Widmalm

  DOI：10.1016/0008-6215(94)00169-3

  日期：1994.10

  syntheses of methyl α- d -mannopyranoside 2-, 3-4-, and 6-phosphate disodium salts are described. 1H, 13C, and 31P NMR spectra of the four monophosphates were recorded, fully assigned, and compared to nonphosphorylated methyl α- d -mannopyranoside in order to obtain chemical shift changes due to phosphorylation. The magnitude of these changes are up to 0.45 ppm for 1H and 3.0 ppm for 13C NMR spectra. The

  摘要描述了甲基α-d-甘露吡喃糖苷2-，3-4-和6-磷酸二钠盐的合成。记录，完全分配了这四种单磷酸的1H，13C和31P NMR光谱，并将其与未磷酸化的甲基α-d-甘露吡喃糖苷进行比较，以获得由于磷酸化引起的化学位移变化。这些变化的幅度对于1H高达0.45 ppm，对于13C NMR谱高达3.0 ppm。还计算了四种化合物中磷酸基团的优选取向。
• Synthesis of an Inositol Phosphoglycan Fragment found in Leishmania Parasites
  作者：Katinka Ruda、Jan Lindberg、Per J Garegg、Stefan Oscarson、Peter Konradsson

  DOI：10.1016/s0040-4020(00)00239-8

  日期：2000.6

  with 2,3,4,6-tetra-O-benzyl-α-d-glucopyranos-1-yl H-phosphonate to form the protected target molecule 12. Deprotection of 12 by acidic deacetalisation/desilylation and subsequent catalytic hydrogenolysis resulted in cleavage of the anomeric phosphodiester to produce 1. Debenzylation with sodium in liquid ammonia followed by acidic deacetalisation/desilylation gave the target compound 2a.

  的合成1和图2a是使用块合成策略描述。化合物4被用作两个甘露糖衍生物的前体，这两个甘露糖衍生物耦合在一起，形成了双甘露糖苷结构单元。硫代糖苷7与8偶联生成肌醇磷酸聚糖9a，将其选择性脱保护并与2,3,4,6-四-O-苄基-α-d-吡喃葡萄糖-1-基H-膦酸酯反应形成受保护的靶分子12。通过酸性脱缩醛/去甲硅烷基化作用对12进行脱保护并随后进行催化氢解反应，导致端基异构磷酸二酯裂解生成1。在液体氨中用钠脱苄基，然后进行酸性脱缩醛/去甲硅烷基化，得到目标化合物2a。
• Synthesis of methyl 6-(ammonium 2-acetamido-2-deoxy-α-d-glucopyranosyl phosphate)-α-d-mannopyranoside and use of this compound for the determination of N-acetylglucosamine-1-phosphotransferase
  作者：Ragupathy Madiyalakan、Seung-Ho An、Rakesh K. Jain、Khushi L. Matta

  DOI：10.1016/s0008-6215(00)90415-4

  日期：1985.12

  Methyl 6-(ammonium 2-acetamido-2-deoxy-alpha-D-glucopyranosyl phosphate)-alpha-D-mannopyranoside was synthesized and identified by 1H-n.m.r. and 13C-n.m.r. data, acid hydrolysis, and elemental analysis. It was utilized for the determination of UDP-N-acetylglucosamine-1-phosphotransferase in an assay procedure that employed methyl alpha-D-mannopyranoside as an acceptor. The assay product was identified and characterized by thin-layer chromatography with the title reference compound. The present technique does not require [32P]UDP-N-acetylglucosamine, but effectively uses commercially available UDP-[14C]GlcNAc.