5-azideo-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-sorbopyranose | 368452-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-azideo-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-sorbopyranose
• 英文别名: 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose；(5S,6S,7R,8R)-8-azido-2,2-dimethyl-6,7-bis(phenylmethoxy)-1,3,10-trioxaspiro[4.5]decane
• CAS: 368452-24-8
• 化学式: C₂₃H₂₇N₃O₅
• 分子量: 425.484
• InChiKey: CTWDVBOILVTFKU-JFYQVNSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-azideo-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-sorbopyranose 在 镍 咪唑 、 四丁基氟化铵 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 48.0h， 生成 (2R,3R,4R,5R)-3,4-dibenzyloxy-2,5-bis(hydroxymethyl)pyrrolidine
  参考文献：
  名称：

  Polyhydroxylated pyrrolidines. Part II: Highly stereoselective synthesis of partially protected DMDP derivatives from d-fructose

  摘要：

  The readily available 3,4-di-O-benzyl-1,2-O-isopropylidene-beta-D-fructopyranose 2 was straightforwardly transformed into 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-beta-D-fructopyranose 4, after treatment under modified Garegg's conditions followed by reaction of the resulting 3,4-di-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-L-sorbopyranose 3 with sodium azide in DMF. Cleavage of the acetonide of 4 to afford 6 followed by regioselective O-tert-butyldiphenylsilylation at C(1)OH afforded 7. Hydrogenation of 7 proceeded with high stereoselectivity yielding 3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-D-mannitol 1, confirmed by its O-desilylation to 8. Compound 1 was subjected to different N-protection reactions to afford the corresponding N-allyl (1a), N-benzyl (1b), and N-tert-butyloxycarbonyl (1c) derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00369-5
• 作为产物：
  描述：

  3-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose 在 吡啶 、 咪唑 、 sodium azide 、 camphor-10-sulfonic acid 、 碘 、 sodium 、 sodium hydride 、 溶剂黄146 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 169.0h， 生成 5-azideo-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-sorbopyranose
  参考文献：
  名称：

  d-Fructose–l-sorbose interconversions. Access to 5-thio-d-fructose and interaction with the d-fructose transporter, GLUT5

  摘要：

  Epimerisation and subsequent functionalization at C-5 of D-fructopyranose derivatives under Mitsunobu and Garegg's conditions provided efficient access to 5-thio-D-fructose (2) as well as to 5-azido-5-deoxy-1,2-O-isopropylidene-beta -D-fructopyranose (19), a known precursor to 2,5-deoxy-2,5-imino-D-mannitol (3). The interaction of 2 with the D-fructose transporter GLUTS, was found to be weaker than that of D-fructose, a result that suggests involvement of the ring oxygen atom in the recognition of D-fructose by GLUTS. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00153-7

文献信息

• d-Fructose–l-sorbose interconversions. Access to 5-thio-d-fructose and interaction with the d-fructose transporter, GLUT5
  作者：Arnaud Tatibouët、Myriam Lefoix、Jonathan Nadolny、Olivier R Martin、Patrick Rollin、Jing Yang、Geoffrey D Holman

  DOI：10.1016/s0008-6215(01)00153-7

  日期：2001.7

  Epimerisation and subsequent functionalization at C-5 of D-fructopyranose derivatives under Mitsunobu and Garegg's conditions provided efficient access to 5-thio-D-fructose (2) as well as to 5-azido-5-deoxy-1,2-O-isopropylidene-beta -D-fructopyranose (19), a known precursor to 2,5-deoxy-2,5-imino-D-mannitol (3). The interaction of 2 with the D-fructose transporter GLUTS, was found to be weaker than that of D-fructose, a result that suggests involvement of the ring oxygen atom in the recognition of D-fructose by GLUTS. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Polyhydroxylated pyrrolidines. Part II: Highly stereoselective synthesis of partially protected DMDP derivatives from d-fructose
  作者：Isidoro Izquierdo、Marı́a T. Plaza、Francisco Franco

  DOI：10.1016/s0957-4166(02)00369-5

  日期：2002.8

  The readily available 3,4-di-O-benzyl-1,2-O-isopropylidene-beta-D-fructopyranose 2 was straightforwardly transformed into 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-beta-D-fructopyranose 4, after treatment under modified Garegg's conditions followed by reaction of the resulting 3,4-di-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-L-sorbopyranose 3 with sodium azide in DMF. Cleavage of the acetonide of 4 to afford 6 followed by regioselective O-tert-butyldiphenylsilylation at C(1)OH afforded 7. Hydrogenation of 7 proceeded with high stereoselectivity yielding 3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-D-mannitol 1, confirmed by its O-desilylation to 8. Compound 1 was subjected to different N-protection reactions to afford the corresponding N-allyl (1a), N-benzyl (1b), and N-tert-butyloxycarbonyl (1c) derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.