N-{9-[(2S,3S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide

Base Information

• Chemical Name: N-{9-[(2S,3S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide
• CAS No.: 200562-25-0
• Molecular Formula: C₄₃H₄₄N₆O₁₁
• Molecular Weight: 820.856

Synonyms:N-{9-[(2S,3S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide

Chemical Property of N-{9-[(2S,3S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide

Chemical Property:

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Technology Process of N-{9-[(2S,3S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide

There total 8 articles about N-{9-[(2S,3S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide 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:

(3S,4R,5S)-5-Triisopropylsilanyloxymethyl-tetrahydro-furan-2,3,4-triol → N-{9-[(2S,3S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide (200562-25-0)

Guidance literature:

Multi-step reaction with 5 steps

1: CH₂Cl₂; pyridine / 14 h / Ambient temperature

2: 58 percent / BSA, trimethylsilyl triflate / CH₂Cl₂ / 2.5 h / 80 °C

3: 92 percent / conc. aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) (i-Pr)2NEt; 2.) 10N aq. NaOH / 1.) CH₂Cl₂, r.t., 30 min; 2.) CH₂Cl₂, THF, MeOH, 4 deg C, 25 min

5: 1.) (i-Pr)2NEt, Bu₂SnCl₂ / 1.) MeCN, r.t., 90 min; 2.) MeCN, 4 deg C, 3 h

With hydrogenchloride; benzenesulfonamide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1002/hlca.19970800803

Reference yield:

1,2,3-tri-O-benzoyl-5-O-(triisopropylsilyl)-α/β-L-ribose → N-{9-[(2S,3S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide (200562-25-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / BSA, trimethylsilyl triflate / CH₂Cl₂ / 2.5 h / 80 °C

2: 92 percent / conc. aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

3: 1.) (i-Pr)2NEt; 2.) 10N aq. NaOH / 1.) CH₂Cl₂, r.t., 30 min; 2.) CH₂Cl₂, THF, MeOH, 4 deg C, 25 min

4: 1.) (i-Pr)2NEt, Bu₂SnCl₂ / 1.) MeCN, r.t., 90 min; 2.) MeCN, 4 deg C, 3 h

With hydrogenchloride; benzenesulfonamide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/hlca.19970800803

Reference yield:

7-[2',3'-di-O-benzoyl-5'-O-(triisopropylsilyl)-β-L-ribofuranosyl]-N3-isobutyrylguanine (200562-13-6) → N-{9-[(2S,3S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide (200562-25-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 50 percent / BSA, trimethylsilyl triflate / CH₂Cl₂ / 2.5 h / 80 °C

2: 92 percent / conc. aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

3: 1.) (i-Pr)2NEt; 2.) 10N aq. NaOH / 1.) CH₂Cl₂, r.t., 30 min; 2.) CH₂Cl₂, THF, MeOH, 4 deg C, 25 min

4: 1.) (i-Pr)2NEt, Bu₂SnCl₂ / 1.) MeCN, r.t., 90 min; 2.) MeCN, 4 deg C, 3 h

With hydrogenchloride; benzenesulfonamide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/hlca.19970800803

upstream raw materials:

<(2-Nitrobenzyl)oxy>methyl chloride

N-(9-{(2S,3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-isobutyramide

4,4'-dimethoxytrityl chloride

9-[2',3'-di-O-benzoyl-5'-O-(triisopropylsilyl)-β-L-ribofuranosyl]-N³-isobutyrylguanine

Downstream raw materials:

Heptanedioic acid (2S,3S,4S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-3-yl ester 4-nitro-phenyl ester

Diisopropyl-phosphoramidous acid (2S,3S,4S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

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