Diethyl 2,6-anhydro-1-deoxy-3,4,5,7-tetra-O-benzyl-L-glycero-D-gluco-heptulopyranose-1-phosphonate | 82701-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Diethyl 2,6-anhydro-1-deoxy-3,4,5,7-tetra-O-benzyl-L-glycero-D-gluco-heptulopyranose-1-phosphonate
• 英文别名: diethyl-C-(1-deoxy 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)methanephosphonate；(2S,3R,4S,5R,6R)-2-(diethoxyphosphorylmethyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 82701-48-2
• 化学式: C₃₉H₄₇O₈P
• 分子量: 674.771
• InChiKey: QXCFLTRISAMEDI-OCKUFXKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Diethyl 2,6-anhydro-1-deoxy-3,4,5,7-tetra-O-benzyl-L-glycero-D-gluco-heptulopyranose-1-phosphonate 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以71%的产率得到
  参考文献：
  名称：

  Thiophosphate and thiophosphonate analogues of glucose-1-phosphate: synthesis and enzymatic activity with a thymidylyltransferase

  摘要：

  Synthetic methods were investigated for the preparation of O and S-glucosyl thiophosphates and glucosyl 1C-thiophosphonate. Four protected glucosyl thiophosphate compounds were synthesized and characterized as precursors to glucose 1-thiophosphate. The effect of various reaction conditions and the nature of the carbohydrate and thiophosphate protecting groups and how they impact both the yields and alpha/beta diastereoselectivity of the glucosyl thiophosphate products were explored. A novel isomerization from an O-linked to S-linked glucosyl thiophosphate was observed. alpha-D-Glucose-1C-thiophosphonate was synthesized and evaluated as a substrate for the thymidylyltransferase, Cps2L. Tandem mass spectrometric analysis determined the position of sulfur in the sugar nucleotide product. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.007
• 作为产物：
  描述：

  chloro-[[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]mercury 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 Diethyl 2,6-anhydro-1-deoxy-3,4,5,7-tetra-O-benzyl-L-glycero-D-gluco-heptulopyranose-1-phosphonate
  参考文献：
  名称：

  Synthesis of the phosphono-analogue of α-D-glucose 1-phosphate

  摘要：

  报道了2,6-脱水-1-脱氧-L-甘油-D-葡萄糖-庚酮吡喃糖-1-磷酸的合成，这是β-D-葡萄糖-1-磷酸的膦酸类似物，其中在糖的同分异构中心，一个亚甲基取代了一个氧原子。

  DOI：

  10.1039/c39820000470

文献信息

• Enzyme-catalyzed synthesis of isosteric phosphono-analogues of sugar nucleotides
  作者：Stephen A. Beaton、Malcolm P. Huestis、Ali Sadeghi-Khomami、Neil R. Thomas、David L. Jakeman

  DOI：10.1039/b808078j

  日期：——

  Efficient enzymatic syntheses of isosteric phosphono analogues of sugar nucleotides have been accomplished using a thymidylyltransferase.

  利用胸苷酰基转移酶，已经成功实现了糖核苷酸等效磷酸类似物的酶促高效合成。