Acetic acid (2R,3R,5S)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,5S)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 1053482-14-6
• Molecular Formula: C₄₈H₄₄N₆O₉
• Molecular Weight: 848.912

Synonyms:

Chemical Property of Acetic acid (2R,3R,5S)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (2R,3R,5S)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-pyran-3-yl ester

There total 8 articles about Acetic acid (2R,3R,5S)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-pyran-3-yl 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:

benzyl O2,O4-phenylboranediyl-α-D-xylopyranoside (6894-01-5) → Acetic acid (2R,3R,5S)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-pyran-3-yl ester (1053482-14-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Et₃N / 1 h / 25 °C

2.1: NaOMe / methanol / 1 h / 25 °C

2.2: 8.5 g / LiAlH₄ / tetrahydrofuran / 30 h / 24 °C

3.1: 9.5 g / iPr₂NEt; AgNO₃ / CH₂Cl₂ / -78 - 25 °C

4.1: H₂ / Pd(OH)2/C / ethanol / 48 h / 25 °C / 4500.36 Torr

5.1: 16.0 g / pyridine / 25 °C

6.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 0.75 h / 60 °C

6.2: Et₃SiOTf / benzene / 1.5 h / 45 °C

7.1: 9.13 g / Et₄NF*2H₂O; AcOH / acetonitrile / 0.33 h / 25 °C

8.1: AgNO₃ / CH₂Cl₂ / 0.5 h / 25 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; sodium methylate; tetraethylammonium fluoride; silver nitrate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1002/1522-2675(200205)85:5<1443::AID-HLCA1443>3.0.CO;2-U

Reference yield:

benzyl 3-deoxy-α-D-xylopyranoside (112482-91-4) → Acetic acid (2R,3R,5S)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-pyran-3-yl ester (1053482-14-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 9.5 g / iPr₂NEt; AgNO₃ / CH₂Cl₂ / -78 - 25 °C

2.1: H₂ / Pd(OH)2/C / ethanol / 48 h / 25 °C / 4500.36 Torr

3.1: 16.0 g / pyridine / 25 °C

4.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 0.75 h / 60 °C

4.2: Et₃SiOTf / benzene / 1.5 h / 45 °C

5.1: 9.13 g / Et₄NF*2H₂O; AcOH / acetonitrile / 0.33 h / 25 °C

6.1: AgNO₃ / CH₂Cl₂ / 0.5 h / 25 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; tetraethylammonium fluoride; silver nitrate; acetic acid; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In ethanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1002/1522-2675(200205)85:5<1443::AID-HLCA1443>3.0.CO;2-U

Reference yield:

benzyl 4-O-[(tert-butyl)dimethylsilyl]-3-deoxy-α-D-ribopyranoside (457880-53-4) → Acetic acid (2R,3R,5S)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-pyran-3-yl ester (1053482-14-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / Pd(OH)2/C / ethanol / 48 h / 25 °C / 4500.36 Torr

2.1: 16.0 g / pyridine / 25 °C

3.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 0.75 h / 60 °C

3.2: Et₃SiOTf / benzene / 1.5 h / 45 °C

4.1: 9.13 g / Et₄NF*2H₂O; AcOH / acetonitrile / 0.33 h / 25 °C

5.1: AgNO₃ / CH₂Cl₂ / 0.5 h / 25 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; tetraethylammonium fluoride; silver nitrate; acetic acid; palladium dihydroxide; In ethanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1002/1522-2675(200205)85:5<1443::AID-HLCA1443>3.0.CO;2-U

upstream raw materials:

4,4'-dimethoxytrityl chloride

N²-acetyl-9-(3'-deoxy-β-D-ribopyranosyl)-O⁶-(diphenylcarbamoyl)guanine 2'-acetate

benzyl O²,O⁴-phenylboranediyl-α-D-xylopyranoside

benzyl 3-deoxy-α-D-xylopyranoside

Downstream raw materials:

Acetic acid (2R,3R,5S)-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-pyran-3-yl ester

N²-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine

N²-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(2-cyanoethyl diisopropylphosphoramidite)

N²-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(4-nitrophenyl heptanedioate)

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