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

Base Information

• Chemical Name: N-[5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-pyridin-2-yl]-acetamide
• CAS No.: 444811-23-8
• Molecular Formula: C₃₃H₃₄N₂O₅
• Molecular Weight: 538.643
• Mol file: 444811-23-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about N-[5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-pyridin-2-yl]-acetamide 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: 91.0%

acetic anhydride (108-24-7) + 2-amino-5-(2',3,',5'-tri-O-benzyl-β-D-ribofuranosyl)pyridine (183311-61-7) → N-[5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-pyridin-2-yl]-acetamide (444811-23-8)

Guidance literature:

In pyridine; at 20 ℃; for 2h;

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

Reference yield:

5-bromo-2-pyridylamine (1072-97-5) → N-[5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-pyridin-2-yl]-acetamide (444811-23-8)

Guidance literature:

Multi-step reaction with 4 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

4.1: 91 percent / pyridine / 2 h / 20 °C

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

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

Reference yield:

N-(5-bromo-pyridin-2-yl)-4-methoxy-N-(4-methoxy-benzoyl)-benzamide → N-[5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-pyridin-2-yl]-acetamide (444811-23-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / 3 h / -78 °C

1.2: 5 h / -78 - 0 °C

1.3: 64 percent / BF₃*OEt₂; Et₃SiH / CH₂Cl₂ / 12 h / -78 - 20 °C

2.1: 88 percent / TFA / 24 h / 20 °C

3.1: 91 percent / pyridine / 2 h / 20 °C

With n-butyllithium; trifluoroacetic acid; In pyridine;

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

upstream raw materials:

acetic anhydride

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

5-bromo-2-pyridylamine