N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>adenin

Base Information

• Chemical Name: N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>adenin
• CAS No.: 145593-99-3
• Molecular Formula: C₃₉H₃₇N₅O₆
• Molecular Weight: 671.753

Synonyms:N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>adenin

Chemical Property of N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>adenin

Chemical Property:

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Technology Process of N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>adenin

There total 7 articles about N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>adenin 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: 89.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N6-Benzoyl-9-(2',3'-dideoxy-β-D-glucopyranosyl)adenin (145593-87-9) → N6-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>adenin (145593-99-3)

Guidance literature:

With pyridine; tetrabutylammonium perchlorate; for 1.33333h; Ambient temperature;

DOI:10.1002/hlca.19920750503

Reference yield:

(+)-[(2R,3S,6S)-2-(benzoyloxymethyl)-6-methoxyoxan-3-yl] benzoate (145593-73-3) → N6-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>adenin (145593-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 35 percent / 1a) hexamethyldisilazane, 1b) chlorotrimethylsilane, 2) SnCl₄ / acetonitrile / 20 h / Ambient temperature

2: 85 percent / 2N aq. NaOH / tetrahydrofuran; methanol; H₂O / 0.33 h / 0 °C

3: 89 percent / pyridine / (Bu₄N)ClO₄ / 1.33 h / Ambient temperature

With pyridine; sodium hydroxide; chloro-trimethyl-silane; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; tetrabutylammonium perchlorate; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1002/hlca.19920750503

Reference yield:

methyl 2,3-dideoxy-α,β-D-erythro-hexopyranoside (23339-18-6) → N6-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>adenin (145593-99-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / r.t.

2: 35 percent / 1a) hexamethyldisilazane, 1b) chlorotrimethylsilane, 2) SnCl₄ / acetonitrile / 20 h / Ambient temperature

3: 85 percent / 2N aq. NaOH / tetrahydrofuran; methanol; H₂O / 0.33 h / 0 °C

4: 89 percent / pyridine / (Bu₄N)ClO₄ / 1.33 h / Ambient temperature

With pyridine; sodium hydroxide; chloro-trimethyl-silane; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; tetrabutylammonium perchlorate; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1002/hlca.19920750503

upstream raw materials:

4,4'-dimethoxytrityl chloride

N⁶-Benzoyl-9-(2',3'-dideoxy-β-D-glucopyranosyl)adenin

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

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

Downstream raw materials:

Succinic acid mono-{(2R,3S,6R)-6-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-3-yl} ester

N⁶-Benzoyl-9-<2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>adenin

N⁶-Benzoyl-9-<2',3'-dideoxy-4'-O-<(diisopropylamino)(methoxy)phosphino>-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>adenin

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