methyl 6-acetamido-7,8,10-tri-O-acetyl-5,9-anhydro-2,3,4,6-tetradeoxy-2-(tert-butoxycarbonylamino)-D-erythro-L-galacto-deconate | 207863-67-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 6-acetamido-7,8,10-tri-O-acetyl-5,9-anhydro-2,3,4,6-tetradeoxy-2-(tert-butoxycarbonylamino)-D-erythro-L-galacto-deconate
• 英文别名: (2R,3S,4R,5S,6S)-5-acetamido-2-(acetoxymethyl)-6-((S)-3-((tertbutoxycarbonyl)amino)-4-methoxy-4-oxobutyl)tetrahydro-2Hpyran-3,4-diyl diacetate；β-C-GlcNAc Ser；methyl (2S)-4-[(2S,3S,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 207863-67-0
• 化学式: C₂₄H₃₈N₂O₁₂
• 分子量: 546.572
• InChiKey: OOGMZZRRAGPXCW-OXVGXARHSA-N

物化性质

• 沸点：
  669.2±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  182
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 6-acetamido-7,8,10-tri-O-acetyl-5,9-anhydro-2,3,4,6-tetradeoxy-2-(tert-butoxycarbonylamino)-D-erythro-L-galacto-deconate 在 sodium hydroxide 、 水 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 18.5h， 生成 (S)-4-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-amino-butyric acid
  参考文献：
  名称：

  Synthesis of the C-Analog of 2-Acetylamino-2-deoxy-β-d-glucopyranosyl l- and d-Serine

  摘要：

  DOI：

  10.1055/s-1998-4490
• 作为产物：
  描述：

  (2S,6S,7R,8R,9R,Z)-methyl 7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate 在 吡啶 、 sodium tetrahydroborate 、 叠氮磷酸二苯酯 、 palladium 10% on activated carbon 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 mercury(II) trifluoroacetate 、 戴斯-马丁氧化剂 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 60.0h， 生成 methyl 6-acetamido-7,8,10-tri-O-acetyl-5,9-anhydro-2,3,4,6-tetradeoxy-2-(tert-butoxycarbonylamino)-D-erythro-L-galacto-deconate
  参考文献：
  名称：

  Synthesis of β-C-GlcNAc Ser from β-C-Glc Ser

  摘要：

  The glycosylation of proteins, specifically installation of O-GlcNAc on Ser/Thr residues, is a dynamic control element for transcription repression, protein degradation, and nutrient sensing. To provide homogeneous and stable structures with this motif, the synthesis of a C-linked mimic, C-GlcNAc Ser, has been prepared from the C-Glc Ser by a double inversion strategy using azide to insert the C-2 nitrogen functionality. The C-Glc Ser was available by a ring-closing metathesis and hydroalkoxylation route.

  DOI：

  10.1021/jo401044x

文献信息

• Expeditious Synthesis of β-Linked Glycosyl Serine Methylene Isosteres (β-C-Gly Ser) via Ethynylation of Sugar Lactones
  作者：Alessandro Dondoni、Giandomenico Mariotti、Alberto Marra、Alessandro Massi

  DOI：10.1055/s-2001-18058

  日期：——

  The addition of the lithium derivative of N-Boc 4-ethynyl-2,2-dimethyl-1,3-oxazolidine to tetra-O-benzyl-d-gluco- and galactonolactone and 2-azido-2-deoxy congeners afforded the corresponding ethynyl ketoses in fairly good yields (64-78%). Following the conversion of the ketoses into O-acetates and removal of the acetoxy group by silane reduction, the resulting β-linked ethynyl glycosides were transformed into N-Boc C-glycosyl α-aminobutyric acids by reduction of the triple bond using H2/Pd(OH)2 and oxidative cleavage of the oxazolidine ring using the Jones’ reagent. After the removal of O-benzyl groups of the carbohydrate moieties by hydrogenation and the reduction of azido to amino group, all compounds were subjected to acetylation and isolated as O- and N-acetyl derivatives. The C-glycosyl α-amino acids prepared correspond to methylene isosteres of O-glycosyl serines.

  将N-Boc 4-乙炔基-2,2-二甲基-1,3-噁唑烷的锂衍生物与四-O-苄基-d-葡萄糖和d-半乳糖内酯以及2-叠氮-2-脱氧同系物反应，得到相应的乙炔基酮，产率相当不错（64-78%）。在将酮转化为O-醋酸酯并通过硅烷还原去除醋酸氧基后，得到的β-连接乙炔基糖苷通过使用H2/Pd(OH)2还原三重键和利用琼斯试剂氧化开环将噁唑烷环转化为N-Boc C-糖苷 α-氨基丁酸。在通过氢化去除糖部分的O-苄基后，并将叠氮基还原为氨基后，所有化合物均经过醋酸化处理，并以O-和N-醋酸衍生物的形式分离出来。所制备的C-糖苷 α-氨基酸对应于O-糖苷丝氨酸的亚甲基等构体。