Methyl-2,3-anhydro-6-O-(t-butyldimethylsilyl)-α-D-allopyranosid | 74265-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-2,3-anhydro-6-O-(t-butyldimethylsilyl)-α-D-allopyranosid
• 英文别名: methyl 2,3-anhydro-6-O-(t-butyldimethylsilyl)-α-D-allopyranoside；methyl 2,3-anhydro-6-O-(tert-butyldimethylsilyl)-α-D-allopyranoside；(1R,2S,4R,5R,6R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-5-ol
• CAS: 74265-02-4
• 化学式: C₁₃H₂₆O₅Si
• 分子量: 290.432
• InChiKey: SSNNGFCIVVUUCV-OOCWMUITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.45
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methyl-2,3-anhydro-6-O-(t-butyldimethylsilyl)-α-D-allopyranosid 在 1,1,3,3-四甲基脲 、 lithium bromide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以75%的产率得到(2S,5S)-2-(tert-butyldimethylsilanyloxymethyl)-5-methoxy-2,5-dihydrofuran-3-carbaldehyde
  参考文献：
  名称：

  Molybdopterin Biosynthesis: Trapping an Unusual Purine Ribose Adduct in the MoaA-Catalyzed Reaction

  摘要：

  MoaA/MoaC catalyze a remarkable rearrangement reaction in which guanosine-5'-triphosphate (GTP) is converted to cyclic pyranopterin monophosphate (cPMP). In this reaction, the C8 of GTP is inserted between the C2' and the C3' carbons of the GTP ribose. Previous experiments with GTP isotopomers demonstrated that the ribose C3' hydrogen atom is abstracted by the adenosyl radical. This led to a novel mechanistic proposal involving an intermediate with a bond between the C8 of guanine and C3' of the ribose. This paper describes the use of 2',3'-dideoxyGTP to trap this intermediate.

  DOI：

  10.1021/ja4041048
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 Methyl-2,3-anhydro-6-O-(t-butyldimethylsilyl)-α-D-allopyranosid
  参考文献：
  名称：

  Molybdopterin Biosynthesis: Trapping an Unusual Purine Ribose Adduct in the MoaA-Catalyzed Reaction

  摘要：

  MoaA/MoaC catalyze a remarkable rearrangement reaction in which guanosine-5'-triphosphate (GTP) is converted to cyclic pyranopterin monophosphate (cPMP). In this reaction, the C8 of GTP is inserted between the C2' and the C3' carbons of the GTP ribose. Previous experiments with GTP isotopomers demonstrated that the ribose C3' hydrogen atom is abstracted by the adenosyl radical. This led to a novel mechanistic proposal involving an intermediate with a bond between the C8 of guanine and C3' of the ribose. This paper describes the use of 2',3'-dideoxyGTP to trap this intermediate.

  DOI：

  10.1021/ja4041048

文献信息

• Strukturelle Abwandlungen an partiell silylierten Kohlenhydraten mittels Triphenylphosphin/Azodicarbonsäure-diäthylester. 3. Mitteilung [1]
  作者：Hannelore H. Brandstetter、Erich Zbiral

  DOI：10.1002/hlca.19800630203

  日期：1980.3.5

  Structural Modification on Partially Silylated Carbohydrates by Means of Triphenylphosphine/Diethyl Azodicarboxylate

  三苯基膦/偶氮二羧酸二乙酯对部分硅烷化碳水化合物的结构改性
• Jones, Keith; McEvoy, John; Wood, William W., Journal of Chemical Research, Miniprint, 1987, # 7, p. 1774 - 1790
  作者：Jones, Keith、McEvoy, John、Wood, William W.、Scott, Ian L.

  DOI：——

  日期：——
• JONES K.;MCEVOY J.;WOOD W. W.;SCOTT I. L., J. CHEM. RES. SYNOP., 1987, N 7, 213, J. CHEM. RES. MICROFICHE, N 17-19, +
  作者：JONES K.、MCEVOY J.、WOOD W. W.、SCOTT I. L.

  DOI：——

  日期：——