2-Deoxy-L-ribose-anilide

Base Information

• Chemical Name: 2-Deoxy-L-ribose-anilide
• CAS No.: 104578-89-4
• Molecular Formula: C11H15 N O3
• Molecular Weight: 209.24
• Hs Code.: 29329990
• European Community (EC) Number: 600-579-5
• Nikkaji Number: J2.170.472E
• Mol file: 104578-89-4.mol

Synonyms:2-Deoxy-L-ribose-anilide;104578-89-4;(2S,3R)-2-(hydroxymethyl)-5-(phenylamino)tetrahydrofuran-3-ol;2-DEOXY-N-PHENYL-L-ERYTHRO-PENTOFURANOSYLAMINE;OYCBOKNPGJKONC-JKIOLJMWSA-N;2-Deoxy-N-phenyl-L-ribofuranosylamine;(2S,3R)-5-anilino-2-(hydroxymethyl)oxolan-3-ol;W-200723;2-deoxy-n-phenyl-d-erythro-pentofuranosylamine (en)d-erythro-pentofuranosylamine, 2-deoxy-n-phenyl- (en)

Chemical Property of 2-Deoxy-L-ribose-anilide

Chemical Property:

• Refractive Index: 1.631
• Boiling Point: 439.4±45.0 °C(Predicted)
• PKA: 13.81±0.60(Predicted)
• PSA: 61.72000
• Density: 1.305
• LogP: 0.63970
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 209.10519334
• Heavy Atom Count: 15
• Complexity: 194

Purity/Quality:

99% ^*data from raw suppliers

2-Deoxy-L-ribose-anilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1NC2=CC=CC=C2)CO)O
• Isomeric SMILES: C1[C@H]([C@@H](OC1NC2=CC=CC=C2)CO)O

Technology Process of 2-Deoxy-L-ribose-anilide

There total 5 articles about 2-Deoxy-L-ribose-anilide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

aniline (62-53-3) + (4R,5S)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one (38996-14-4) → 2-deoxy-N-phenyl-L-erythro-pentofuranosylamine (104578-89-4)

Guidance literature:

(4R,5S)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one; With 2-methyl-but-2-ene; dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 20h;

aniline; In ethanol; water; at 5 ℃; for 3h;

DOI:10.1016/j.tet.2005.03.001

Reference yield:

methyl (3R,4S)-3-(tert-butyldimethylsiloxy)-4,5-(isopropylidenedioxy)pentanoate (104578-88-3) → 2-deoxy-N-phenyl-L-erythro-pentofuranosylamine (104578-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1: CF₃COOH, H₂O / 3 h / Ambient temperature

2: 1.) disiamylborane / 1.) THF, RT, 20 h, 2.) ethanol, water

With water; bis-(1,2-dimethylpropyl)borane; trifluoroacetic acid;

DOI:10.1021/jo00238a015

Reference yield:

4-cyano-4-deoxy-1,2-O-isopropylidene-D-erythritol (364042-57-9) → 2-deoxy-N-phenyl-L-erythro-pentofuranosylamine (104578-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / sulfuric acid / 1,2-dichloro-ethane; H₂O / 5 h / Heating

2.1: borane-dimethylsulfide complex; 2-methyl-2-butene / tetrahydrofuran / 20 h / 20 °C

2.2: 56 percent / H₂O; ethanol / 3 h / 5 °C

With 2-methyl-but-2-ene; dimethylsulfide borane complex; sulfuric acid; In tetrahydrofuran; water; 1,2-dichloro-ethane;

DOI:10.1016/j.tet.2005.03.001

upstream raw materials:

(4R,5S)-5-(hydroxymethyl)tetrahydrofuran-2,4-diol

aniline

(4R,5S)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

4-cyano-4-deoxy-1,2-O-isopropylidene-D-erythritol

Refernces

• 1、 Kita, Yasuyuki,Tamura, Osamu,Itoh, Fumio,Yasuda, Hitoshi,Kishino, Hiroko,et al.. "Chemistry of O-Silylated Ketene Acetals: Stereocontrolled Synthesis of 2-Deoxy- and 2-Deoxy-2-C-alkyl-erythro-pentoses". . p. 554 - 561. Retrieved 2007/10/02.