9-<4'-O-<(2-Cyanoethoxy)(diisopropylamino)phosphino>-2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>-N²-isobutyrylguanin

Base Information

• Chemical Name: 9-<4'-O-<(2-Cyanoethoxy)(diisopropylamino)phosphino>-2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>-N²-isobutyrylguanin
• CAS No.: 145594-09-8
• Molecular Formula: C₄₅H₅₆N₇O₈P
• Molecular Weight: 853.956

Synonyms:

Chemical Property of 9-<4'-O-<(2-Cyanoethoxy)(diisopropylamino)phosphino>-2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>-N²-isobutyrylguanin

Chemical Property:

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Technology Process of 9-<4'-O-<(2-Cyanoethoxy)(diisopropylamino)phosphino>-2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>-N²-isobutyrylguanin

There total 12 articles about 9-<4'-O-<(2-Cyanoethoxy)(diisopropylamino)phosphino>-2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>-N²-isobutyrylguanin 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:

4,4'-dimethoxytrityl chloride (40615-36-9) → 9-<4'-O-<(2-Cyanoethoxy)(diisopropylamino)phosphino>-2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>-N2-isobutyrylguanin (145594-09-8,145610-79-3)

Guidance literature:

Multi-step reaction with 2 steps

2: 69 percent / (i-Pr)2EtN / tetrahydrofuran / 1 h / Ambient temperature

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1002/hlca.19920750503

Reference yield:

(+)-[(2R,3S,6S)-2-(benzoyloxymethyl)-6-methoxyoxan-3-yl] benzoate (145593-73-3) → 9-<4'-O-<(2-Cyanoethoxy)(diisopropylamino)phosphino>-2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>-N2-isobutyrylguanin (145594-09-8,145610-79-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) CF₃SO₃SiMe₃, BSA, 2) 2N NaOH (aqueous) / 1) acetonitrile, 80 deg C, 16 h, 2) THF/MeOH/H₂O (5:4:1), 0 deg C, 25 min

2: 63 percent / pyridine / (Bu₄N)ClO₄ / 1 h / Ambient temperature

3: 69 percent / (i-Pr)2EtN / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; benzenesulfonamide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; tetrabutylammonium perchlorate; In tetrahydrofuran;

DOI:10.1002/hlca.19920750503

Reference yield:

methyl 2,3-dideoxy-α,β-D-erythro-hexopyranoside (23339-18-6) → 9-<4'-O-<(2-Cyanoethoxy)(diisopropylamino)phosphino>-2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>-N2-isobutyrylguanin (145594-09-8,145610-79-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / r.t.

2: 1) CF₃SO₃SiMe₃, BSA, 2) 2N NaOH (aqueous) / 1) acetonitrile, 80 deg C, 16 h, 2) THF/MeOH/H₂O (5:4:1), 0 deg C, 25 min

3: 63 percent / pyridine / (Bu₄N)ClO₄ / 1 h / Ambient temperature

4: 69 percent / (i-Pr)2EtN / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; benzenesulfonamide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; tetrabutylammonium perchlorate; In tetrahydrofuran;

DOI:10.1002/hlca.19920750503

upstream raw materials:

(+)-[(2R,3S,6S)-2-(benzoyloxymethyl)-6-methoxyoxan-3-yl] benzoate

3-deoxy-β-D-glucose

methyl 2,3-dideoxy-α,β-D-erythro-hexopyranoside

methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside

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