2-phenyl-4,5-(5,6-isopropylidene-D-glucofurano)-1,3-oxazoline | 23661-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenyl-4,5-(5,6-isopropylidene-D-glucofurano)-1,3-oxazoline
• 英文别名: (3aR)-5c-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenyl-(3ar,6ac)-3a,5,6,6a-tetrahydro-furo[3,2-d]oxazol-6c-ol；2-amino-O⁵,O⁶-isopropylidene-O¹,N-phenylmethanylylidene-α-D-2-deoxy-glucofuranose；2-Phenyl-5',6'-O-isopropyliden-α-D-glucofurano<1',2'-5,4>Δ²-oxazolin, 2-Desoxy-2-amino-1-O-2-N-benzylidin-5,6-O-isopropyliden-α-D-glucofuranosid；(3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenyl-3a,5,6,6a-tetrahydrofuro[3,2-d][1,3]oxazol-6-ol
• CAS: 23661-45-2
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: GRTJSQNBKOOWFS-FTQJZPFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-phenyl-4,5-(5,6-isopropylidene-D-glucofurano)-1,3-oxazoline 在 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三正丁基氢锡 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 45.5h， 生成 β-methyl-2-benzoylamino-2,3-didesoxy-D-ribofuranoside
  参考文献：
  名称：

  ?-Methyl-2-amino-2,3-didesoxyribofuranoside, a Novel Building Block for Backbone Modified Antisense Oligonucleotides

  摘要：

  A synthesis of the amino sugar 2-amino-2,3-didesoxyribose is described. Starting from D-glucosamine, beta-methylfuranoside was obtained in eight steps in 20% yield. This carbohydrate is a novel building block for nucleosides and for backbone modified antisense oligonucleotides with 2'-5' amide linkages.

  DOI：

  10.1007/s00706-003-0086-1
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 sodium methylate 、 三氯化铁 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-phenyl-4,5-(5,6-isopropylidene-D-glucofurano)-1,3-oxazoline
  参考文献：
  名称：

  ?-Methyl-2-amino-2,3-didesoxyribofuranoside, a Novel Building Block for Backbone Modified Antisense Oligonucleotides

  摘要：

  A synthesis of the amino sugar 2-amino-2,3-didesoxyribose is described. Starting from D-glucosamine, beta-methylfuranoside was obtained in eight steps in 20% yield. This carbohydrate is a novel building block for nucleosides and for backbone modified antisense oligonucleotides with 2'-5' amide linkages.

  DOI：

  10.1007/s00706-003-0086-1

文献信息

• The allyl ether as a protecting group in carbohydrate chemistry. Part III. The but-2-enyl ether group
  作者：Patricia A. Gent、Roy Gigg、R. Conant

  DOI：10.1039/p19720001535

  日期：——

  2,4,6-Tri-O-benzyl-D-galactopyranose was prepared from allyl 3-O-allyl-2,4,6-tri-O-benzyl-α-D-galactopyranoside for use in the synthesis of oligosaccharides containing a galactose residue substituted on the 3-position. The use of the but-2-enyl (crotyl) ether system for the protection of hydroxy-groups was investigated. The but-2-enyl ethers were stable to mild acid hydrolysis and to the basic conditions

  -2,4,6-三ö苄基d -galactopyranose由烯丙基3-制备ø -烯丙基-2,4,6-三ö苄基α- d -galactopyranoside用于寡糖合成使用含有在3位上取代的半乳糖残基。研究了丁-2-烯基（巴豆基）醚体系用于保护羟基的用途。丁-2-烯基醚对于温和的酸水解和苄基化所需的基本条件均稳定，并易于在叔丁醇钾的二甲基亚砜中裂解。由烯丙基2,4,6-三-O-苄基-3- O制备丙-1-烯基2,4,6-三-O-苄基-α- D-吡喃半乳糖苷-丁-2-烯基- α- d -galactopyranoside和丙-1-烯基2-苯甲酰氨基-4,6-二ø -苄基-2-脱氧β- d吡喃葡萄糖苷，从烯丙基2-苯甲酰氨基4制备，6-二-O-苄基-3- O-丁-2-烯基-2-脱氧-β - D-吡喃葡萄糖苷。由相应的β-烯丙基糖苷制备2-苯甲酰胺基-3,4,6-三-O-苄基-2-脱氧-D-葡萄糖-和D-半乳糖-吡喃糖。
• Structural modifications of antisense oligonucleotides
  作者：Ernst Urban、Christian R. Noe

  DOI：10.1016/s0014-827x(03)00022-3

  日期：2003.3

  Antisense oligonucleotides are efficient tools for the inhibition of gene expression in a sequence specific way. Natural oligonucleotides are decomposed rapidly in biological systems, which strongly restrict their application. In contrast, artificial oligonucleotides are designed to be more stable against degradation than the target mRNA, which results in a catalytic effect of the drug. Modification of the phosphate linkage has been the first successful strategy for antisense drug developments and Fomivirsene the first antisense drug in therapy. The launch of Fomivirsene has resulted in a revolutionary spin off to antisense research leading to a second generation of antisense oligonucleotides, which are stable against oligonucleotide cleaving enzymes. Among these, oligonucleotides bearing an alkoxy substituent in position 2' were the most successful ones. The third generation of antisense oligonucleotides contains structure elements, which enhance the antisense action. Zwitterionic oligonucleotides show remarkable results, first, because the stability against ribozymes is largely increased, and secondly, because the electrostatic repulsion between the anionic sense and the zwitterionic antisense cords is minimized. Promising new target molecules in antisense research are oligonucleotide chimäres, which enhance the antisense action (chimäres with intercalators, chelators or polyamines) or enable an application as sequence specific detectors (chimäres with biotin, fluorescein or radioligands).
• Kunz, Horst; Schmidt, Peter, Liebigs Annalen der Chemie, 1982, # 7, p. 1245 - 1260
  作者：Kunz, Horst、Schmidt, Peter

  DOI：——

  日期：——
• A convenient route to alkyl 2-benzamido-4,6-O-benzylidene-2-deoxy-β-d-glucopyranosides
  作者：Roy Gigg、Robert Conant

  DOI：10.1016/s0008-6215(00)81056-3

  日期：——
• Konstas et al., Chemische Berichte, 1959, vol. 92, p. 1288,1292
  作者：Konstas et al.

  DOI：——

  日期：——