2-amino-5-(2',3,',5'-tri-O-benzyl-β-D-ribofuranosyl)pyridine

Base Information

• Chemical Name: 2-amino-5-(2',3,',5'-tri-O-benzyl-β-D-ribofuranosyl)pyridine
• CAS No.: 183311-61-7
• Molecular Formula: C₃₁H₃₂N₂O₄
• Molecular Weight: 496.606
• Mol file: 183311-61-7.mol

Synonyms:2-amino-5-(2',3,',5'-tri-O-benzyl-β-D-ribofuranosyl)pyridine

Chemical Property of 2-amino-5-(2',3,',5'-tri-O-benzyl-β-D-ribofuranosyl)pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-amino-5-(2',3,',5'-tri-O-benzyl-β-D-ribofuranosyl)pyridine

There total 5 articles about 2-amino-5-(2',3,',5'-tri-O-benzyl-β-D-ribofuranosyl)pyridine 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: 88.0%

N-[5-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-pyridin-2-yl]-4-methoxy-N-(4-methoxy-benzoyl)-benzamide → 2-amino-5-(2',3,',5'-tri-O-benzyl-β-D-ribofuranosyl)pyridine (183311-61-7)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(02)00481-1

Reference yield:

5-bromo-2-pyridylamine (1072-97-5) → 2-amino-5-(2',3,',5'-tri-O-benzyl-β-D-ribofuranosyl)pyridine (183311-61-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 64 percent / NaH / dimethylformamide / 6 h / 20 °C

2.1: n-BuLi / 3 h / -78 °C

2.2: 5 h / -78 - 0 °C

2.3: 64 percent / BF₃*OEt₂; Et₃SiH / CH₂Cl₂ / 12 h / -78 - 20 °C

3.1: 88 percent / TFA / 24 h / 20 °C

With n-butyllithium; sodium hydride; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)00481-1

Reference yield:

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one (14233-64-8,134307-32-7,55094-52-5) + 5-bromo-2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)pyridine (183311-60-6) → 2-amino-5-(2',3,',5'-tri-O-benzyl-β-D-ribofuranosyl)pyridine (183311-61-7)

Guidance literature:

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; Yield given. Multistep reaction; 1.) THF, -75 deg C, 3 h, -75 deg C -> 0 deg C, 4 h, 2.) CH2Cl2, -75 deg C -> rt, overnight;

DOI:10.1021/ja9704904

upstream raw materials:

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

5-bromo-2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)pyridine

5-bromo-2-pyridylamine

Downstream raw materials:

2-(N-benzoylamino)-5-(β-D-ribofuranosyl)pyridine

N-[5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-pyridin-2-yl]-acetamide

Thiocarbonic acid O-[(2S,3S,3aR,9aR)-2-(6-benzoylamino-pyridin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-p-tolyl ester

N-(5-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-pyridin-2-yl)-benzamide