[(2S,3R,4R)-2,3,4-triacetyloxy-5-trityloxypentyl] acetate | 192133-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [(2S,3R,4R)-2,3,4-triacetyloxy-5-trityloxypentyl] acetate
• CAS: 192133-09-8
• 化学式: C₃₂H₃₄O₉
• 分子量: 562.617
• InChiKey: WNYGTPGDKDGNIK-YPKYBTACSA-N

物化性质

• 沸点：
  595.1±50.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R)-2,3,4-triacetyloxy-5-trityloxypentyl] acetate 在 甲酸 作用下， 以 水 为溶剂， 反应 0.12h， 以90%的产率得到1,2,3,4-tetra-O-acetyl-D-ribitol
  参考文献：
  名称：

  Synthesis and Testing of New Modified Nucleosides

  摘要：

  New efficient routes for the high-yielding synthesis of several classes of modified nucleosides have been developed. We have prepared both the D- and L-enantiomers of the methylene-expanded oxetanocin isonucleosides 1a-e and the L-2',3'-dideoxy isonucleosides 2abc (both the oxa and thia analgoues) as well as new routes for the preparation of L-ribose and 2-deoxy L-ribose 3ab and their modified nucleosides 4.

  DOI：

  10.1080/15257779908041490
• 作为产物：
  描述：

  5-O-三苯甲基-D-呋喃核糖 在 sodium tetrahydroborate 作用下， 以 吡啶 为溶剂， 生成 [(2S,3R,4R)-2,3,4-triacetyloxy-5-trityloxypentyl] acetate
  参考文献：
  名称：

  Synthesis and Testing of New Modified Nucleosides

  摘要：

  New efficient routes for the high-yielding synthesis of several classes of modified nucleosides have been developed. We have prepared both the D- and L-enantiomers of the methylene-expanded oxetanocin isonucleosides 1a-e and the L-2',3'-dideoxy isonucleosides 2abc (both the oxa and thia analgoues) as well as new routes for the preparation of L-ribose and 2-deoxy L-ribose 3ab and their modified nucleosides 4.

  DOI：

  10.1080/15257779908041490

文献信息

• Efficient syntheses of l-ribose and 2-deoxy l-ribose from d-ribose and l-arabinose
  作者：Michael E. Jung、Yue Xu

  DOI：10.1016/s0040-4039(97)00870-8

  日期：1997.6

  Interconversion of the ends of D-ribose 2 afforded in 6 steps and 45% overall yield L-ribose 1, from which 2-deoxy L-ribose 12 was easily prepared. In addition, the inexpensive L-arabinose 13 was also converted into 2-deoxy L-ribose 12 via a reductive radical rearrangement of the arabinopyranosyl bromide 14. (C) 1997 Elsevier Science Ltd.
• Yarrowia lipolytica dehydrogenase/reductase: An enzyme tolerant for lipophilic compounds and carbohydrate substrates
  作者：Kamila Napora、Tanja M. Wrodnigg、Patrick Kosmus、Martin Thonhofer、Karen Robins、Margit Winkler

  DOI：10.1016/j.bmcl.2013.03.064

  日期：2013.6

  Yarrowia lipolytica short chain dehydrogenase/reductase (YlSDR) was expressed in Escherichia coli, purified and characterized in vitro. The substrate scope for YlSDR mediated oxidation was investigated with alcohols and unprotected carbohydrates spectrophotometrically, revealing a preference for secondary compared to primary alcohols. In reduction direction, YlSDR was highly active on ribulose and fructose, suggesting that the enzyme is a mannitol-2-dehydrogenase. In order to explore substrate tolerance especially for space-demanding, lipophilic protecting groups, 5-O-trityl-D-ribitol and 5-O-trityl-alpha,beta-D-ribose were investigated as substrates: YlSDR oxidized 5-O-trityl-D-ribitol and 5-O-trityl-alpha,beta-D-ribose and reduced the latter at the expense of NADP(H). (C) 2013 Elsevier Ltd. All rights reserved.
• [EN] SYNTHESIS OF L-RIBOSE AND 2-DEOXY L-RIBOSE<br/>[FR] SYNTHESE DE L-RIBOSE ET 2-DESOXY L-RIBOSE
  申请人：——

  公开号：WO1998039347A2

  公开（公告）日：1998-09-11

  [EN] A method for synthesizing L-ribose (1) and 2-deoxy L-ribose (12) from inexpensive D-ribose (2) is provided. The 5-O-trityl ribose (3) (prepared in 70 % yield from D-ribose) is reduced with borohydride to give the tetrol (4), which is then peracetylated to the tetraacetate (5). Hydrolysis of the trityl ether followed by Swern oxidation affords the aldehyde (7) via the alcohol (6). This aldehyde is a protected form of L-ribose, being L-ribose 2,3,4,5,-tetraacetate. Mild basic hydrolysis of the acetate affords L-ribose itself (1), thus ending an efficient six-step synthesis of (1) from (2) which proceeds in 39 % overall yield. In a second aspect of the invention, L-ribose is converted into the beta -selenophenyl ribofuranoside (10) via the tetraester (9) in 71 % isolated yield for the four steps. Treatment of (10) with tributylstannane and AIBN furnishes in 84 % yield the tribenzoyl 2-deoxy-L-ribofuranoside (11) which, on basic hydrolysis, gives 2-deoxy L-ribose (12) in high yield. In a third aspect of the invention, L-arabinose (13) is converted into 2-deoxy L-ribose (12) via the arabinopyranosyl bromide (14), via similar reductive rearrangement with tributylstannane to give the 2-deoxy ribopyranose tribenzoate (16). Hydrolysis yields 2-deoxy L-ribose. In a third aspect of the invention, L-arabinose is converted into 2-deoxy L-ribose by an alternate route.
  [FR] La présente invention concerne un procédé de synthèse de L-ribose (1) et de 2-désoxy L-ribose (12) à partir de D-ribose (2) peu coûteuse. La 5-O-trityl ribose (3) (préparée à 70 % à partir de D-ribose) est réduite avec du borohydrure de façon à obtenir le trétol (4) qui est ensuite peracétylé pour former le tétraacétate (5). L'hydrolyse de l'éther de trityle suivie par une oxydation de Swern produit l'aldhéhyde (7) à l'aide de l'alcool (6). Cet aldéhyde est une forme protégée de L-ribose qui est un L-ribose 2,3,4,5,-tétraacétate. L'hydrolyse faiblement basique de l'acétate produit L-ribose lui-même (1), terminant ainsi une synthèse efficace en six-sept étapes de (1) à partir de (2), qui produit un rendement global de 39 %. Selon un second mode de réalisation de l'invention, L-ribose est converti en beta -sélénophényl-ribofuranoside (10) à l'aide du tétraester (9) dans un rendement isolé de 71 % pour les quatre étapes. Un traitement de (10) avec du tributylstannane et AIBN produit le tribenzoyl-2-désoxy-L-ribofuranoside (11) dans un rendement de 84 %, qui dans une hydrolyse de base produit 2-désoxy L-ribose (12) dans un rendement élevé. Selon un troisième mode de réalisation de l'invention, L-arabinose (13) est converti en 2-désoxy L-ribose (12) par le bromure d'arabinopyranosyle (14) à l'aide d'un réarrangement réducteur avec le tributylstannane de façon à obtenir le 2-désoxy ribopyranose tribenzoate (16). L'hydrolyse produit 2-désoxy L-ribose. Selon un troisième mode de réalisation de l'invention, L-arabinose est converti en 2-désoxy L-ribose par un autre processus.