3,5-dichloro-2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine

Base Information

• Chemical Name: 3,5-dichloro-2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine
• CAS No.: 181581-94-2
• Molecular Formula: C₃₀H₂₈Cl₂N₂O₄
• Molecular Weight: 551.469
• Mol file: 181581-94-2.mol

Synonyms:3,5-dichloro-2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine

Chemical Property of 3,5-dichloro-2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-dichloro-2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine

There total 2 articles about 3,5-dichloro-2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine 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: 93.0%

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-2-(3,5-dichloro-pyrazin-2-yl)-tetrahydro-furan-2-ol (181581-98-6) → 3,5-dichloro-2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine (181581-94-2)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; -78 deg C, RT, 5d;

DOI:10.1016/0040-4039(96)01121-5

Reference yield:

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one (14233-64-8,134307-32-7,55094-52-5) → 3,5-dichloro-2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine (181581-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / n-BuLi, 2,2,6,6-tetramethylpiperidine / tetrahydrofuran / -78 deg C, 3 h; RT, 10 h

2: 93 percent / BF₃*OEt₂, Et₃SiH / CH₂Cl₂ / -78 deg C, RT, 5d

With 2,2,6,6-tetramethyl-piperidine; triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(96)01121-5

Reference yield:

ethyl cyanoformate (623-49-4) + 3,5-dichloro-2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine (181581-94-2) → ethyl 3,5-dichloro-6-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine-2-carboxylate (199847-34-2)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; Yield given; Multistep reaction; 1.) THF, hexane, -94 deg C, 120 min, 2.) THF, hexane, 60 min;

DOI:10.1021/jm970532z

upstream raw materials:

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-2-(3,5-dichloro-pyrazin-2-yl)-tetrahydro-furan-2-ol

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one

Downstream raw materials:

ethyl 3,5-dichloro-6-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazine-2-carboxylate