(3R,6S)-(6-[2-(6-methoxy-[1,5]naphthyridin-4-yl)acetyl]tetrahydro-pyran-3-yl)carbamic acid benzyl ester

Base Information

• Chemical Name: (3R,6S)-(6-[2-(6-methoxy-[1,5]naphthyridin-4-yl)acetyl]tetrahydro-pyran-3-yl)carbamic acid benzyl ester
• CAS No.: 881657-93-8
• Molecular Formula: C₂₄H₂₅N₃O₅
• Molecular Weight: 435.48

Synonyms:(3R,6S)-(6-[2-(6-methoxy-[1,5]naphthyridin-4-yl)acetyl]tetrahydro-pyran-3-yl)carbamic acid benzyl ester

Chemical Property of (3R,6S)-(6-[2-(6-methoxy-[1,5]naphthyridin-4-yl)acetyl]tetrahydro-pyran-3-yl)carbamic acid benzyl ester

Chemical Property:

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Technology Process of (3R,6S)-(6-[2-(6-methoxy-[1,5]naphthyridin-4-yl)acetyl]tetrahydro-pyran-3-yl)carbamic acid benzyl ester

There total 9 articles about (3R,6S)-(6-[2-(6-methoxy-[1,5]naphthyridin-4-yl)acetyl]tetrahydro-pyran-3-yl)carbamic acid benzyl ester 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: 67.0%

(3R,6S)-[6-(6-methoxy-[1,5]naphthyridin-4-ylethynyl)tetrahydro-pyran-3-yl]carbamic acid benzyl ester → (3R,6S)-(6-[2-(6-methoxy-[1,5]naphthyridin-4-yl)acetyl]tetrahydro-pyran-3-yl)carbamic acid benzyl ester (881657-93-8)

Guidance literature:

With sulfuric acid; mercury(II) oxide; In tetrahydrofuran; methanol; water; at 55 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jm501590q

Reference yield: 60.0%

→ (3R,6S)-(6-[2-(6-methoxy-[1,5]naphthyridin-4-yl)acetyl]tetrahydro-pyran-3-yl)carbamic acid benzyl ester (881657-93-8)

Guidance literature:

Reference yield:

6-methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate (394223-86-0) → (3R,6S)-(6-[2-(6-methoxy-[1,5]naphthyridin-4-yl)acetyl]tetrahydro-pyran-3-yl)carbamic acid benzyl ester (881657-93-8)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere

2: trifluoroacetic acid / 0.17 h / 20 °C / Inert atmosphere

3: sodium hydrogencarbonate / ethyl acetate; water / 0.5 h / Inert atmosphere

4: mercury(II) oxide; sulfuric acid / water; methanol; tetrahydrofuran / 4 h / 55 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sulfuric acid; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; mercury(II) oxide; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm501590q

upstream raw materials:

6-methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate

benzyl chloroformate

tert-butyl ((3R,6S)-6-ethynyltetrahydro-2H-pyran-3-yl)carbamate

{(3R,6S)-6-[(1R)-1-hydroxy-2-(6-methoxy[1,5]naphthyridin-4-yl)-ethyl]-tetrahydropyran-3-yl}-carbamic acid tert-butyl ester

Downstream raw materials:

C₂₄H₂₈N₄O₄

C₂₉H₃₆N₄O₆

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