6-N-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hex-5-enofuranosyl)adenine

Base Information

• Chemical Name: 6-N-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hex-5-enofuranosyl)adenine
• CAS No.: 38930-69-7
• Molecular Formula: C₂₁H₂₁N₅O₄
• Molecular Weight: 407.429
• Mol file: 38930-69-7.mol

Synonyms:6-N-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hex-5-enofuranosyl)adenine

Chemical Property of 6-N-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hex-5-enofuranosyl)adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-N-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hex-5-enofuranosyl)adenine

There total 8 articles about 6-N-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hex-5-enofuranosyl)adenine 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: 60.0%

N-{9-[(3aR,4R,6R,6aR)-2,2-Dimethyl-6-((E)-2-tributylstannanyl-vinyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-benzamide → 5'-deoxy-2',3'-O-isopropylidene-5'-methyleneadenosine (65969-38-2) + 6-N-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hex-5-enofuranosyl)adenine (38930-69-7)

Guidance literature:

With ammonium fluoride; In ethanol; for 14h; Heating;

DOI:10.1021/jm00047a015

Reference yield:

Methyltriphenylphosphonium bromide (1779-49-3) + 6-N-benzoyl-9-(2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,5-furanosyl)adeninehydrate (43077-04-9) → 6-N-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hex-5-enofuranosyl)adenine (38930-69-7)

Guidance literature:

Methyltriphenylphosphonium bromide; With tert.-butyl lithium; In tetrahydrofuran; at -40 - 0 ℃; for 1h; Inert atmosphere;

6-N-benzoyl-9-(2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,5-furanosyl)adeninehydrate; In benzene; for 2h; Dean-Stark; Reflux;

In tetrahydrofuran; at -40 - 0 ℃; Inert atmosphere;

DOI:10.1039/c4ob02560a

Reference yield:

N-6-benzoyl-2',3'-O-isopropylideneadenosine (39947-04-1) → 6-N-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hex-5-enofuranosyl)adenine (38930-69-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Cl₂CHCO₂H, dicyclohexylcarbodiimide, DMSO / 1.5 h / Ambient temperature

2: 1.) sodium 2-methyl-2-butoxide / 1.) Et₂O, benzene, ambient temperature, 1.5 h, 2.) THF, a) -20 deg C, 2 h, b) ca. 0 deg C, overnight

With dichloro-acetic acid; sodium tert-pentoxide; dimethyl sulfoxide; dicyclohexyl-carbodiimide;

DOI:10.1139/v91-051

upstream raw materials:

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde

Methyltriphenylphosphonium bromide

N-6-benzoyl-2',3'-O-isopropylideneadenosine

2',3'-isopropylidene adenosine

Downstream raw materials:

N-{9-[(3aR,4R,6S,6aS)-6-(1-Bromo-vinyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-benzamide