(Z)-tert-butyl-N-[3-acetamido-4-(2,3,5-tri-O-benzyl-D-ribofuranosylidenemethyl)pyridin-2-yl] carbamate

Base Information

• Chemical Name: (Z)-tert-butyl-N-[3-acetamido-4-(2,3,5-tri-O-benzyl-D-ribofuranosylidenemethyl)pyridin-2-yl] carbamate
• CAS No.: 591751-92-7
• Molecular Formula: C₃₉H₄₃N₃O₇
• Molecular Weight: 665.786
• Mol file: 591751-92-7.mol

Synonyms:(Z)-tert-butyl-N-[3-acetamido-4-(2,3,5-tri-O-benzyl-D-ribofuranosylidenemethyl)pyridin-2-yl] carbamate

Chemical Property of (Z)-tert-butyl-N-[3-acetamido-4-(2,3,5-tri-O-benzyl-D-ribofuranosylidenemethyl)pyridin-2-yl] carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-tert-butyl-N-[3-acetamido-4-(2,3,5-tri-O-benzyl-D-ribofuranosylidenemethyl)pyridin-2-yl] carbamate

There total 1 articles about (Z)-tert-butyl-N-[3-acetamido-4-(2,3,5-tri-O-benzyl-D-ribofuranosylidenemethyl)pyridin-2-yl] carbamate 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: 99.0%

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one (14233-64-8,134307-32-7,55094-52-5) + tert-butyl-N-(3-acetamido-4-methylpyridin-2-yl) carbamate (518038-74-9) → (Z)-tert-butyl-N-[3-acetamido-4-(2,3,5-tri-O-benzyl-D-ribofuranosylidenemethyl)pyridin-2-yl] carbamate (591751-92-7)

Guidance literature:

tert-butyl-N-(3-acetamido-4-methylpyridin-2-yl) carbamate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 5 ℃; for 0.583333h;

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 5.25h;

With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 6h;

DOI:10.1021/jo026715x

Reference yield: 51.0%

(Z)-tert-butyl-N-[3-acetamido-4-(2,3,5-tri-O-benzyl-D-ribofuranosylidenemethyl)pyridin-2-yl] carbamate (591751-92-7) → N-[2-amino-4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)methylpyridin-3-yl]acetamide (591751-93-8) + N-[2-amino-4-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)methylpyridin-3-yl]acetamide

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1021/jo026715x

Reference yield:

(Z)-tert-butyl-N-[3-acetamido-4-(2,3,5-tri-O-benzyl-D-ribofuranosylidenemethyl)pyridin-2-yl] carbamate (591751-92-7) → 2-methyl-7-[(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)methyl]imidazolo[4,5-b]pyridine

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / trifluoroacetic acid; triethylsilane / CH₂Cl₂ / 20 °C

2: 5 percent / toluene / 50 °C

With triethylsilane; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1021/jo026715x

upstream raw materials:

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

tert-butyl-N-(3-acetamido-4-methylpyridin-2-yl) carbamate

Downstream raw materials:

N-[2-amino-4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)methylpyridin-3-yl]acetamide

7-amino-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazolo[3,4-c]pyridine

N-[4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)methyl-2-phthalimidopyridin-3-yl]acetamide