9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N²-(methoxyacetyl)-N⁶-isobutyryl-9H-purine-2,6-diamine 2'(2-cyanoethyl diisopropylphosphoramidite)

Base Information

• Chemical Name: 9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N²-(methoxyacetyl)-N⁶-isobutyryl-9H-purine-2,6-diamine 2'(2-cyanoethyl diisopropylphosphoramidite)
• CAS No.: 457880-66-9
• Molecular Formula: C₄₇H₅₉N₈O₉P
• Molecular Weight: 911.007

Synonyms:9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N²-(methoxyacetyl)-N⁶-isobutyryl-9H-purine-2,6-diamine 2'(2-cyanoethyl diisopropylphosphoramidite)

Chemical Property of 9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N²-(methoxyacetyl)-N⁶-isobutyryl-9H-purine-2,6-diamine 2'(2-cyanoethyl diisopropylphosphoramidite)

Chemical Property:

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Technology Process of 9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N²-(methoxyacetyl)-N⁶-isobutyryl-9H-purine-2,6-diamine 2'(2-cyanoethyl diisopropylphosphoramidite)

There total 15 articles about 9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N²-(methoxyacetyl)-N⁶-isobutyryl-9H-purine-2,6-diamine 2'(2-cyanoethyl diisopropylphosphoramidite) 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: 90.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N6-isobutyryl-N2-(methoxyacetyl)-9H-purine-2,6-diamine (457880-63-6) → 9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N2-(methoxyacetyl)-N6-isobutyryl-9H-purine-2,6-diamine 2'(2-cyanoethyl diisopropylphosphoramidite) (457880-66-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 4h;

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

Reference yield:

benzyl O2,O4-phenylboranediyl-α-D-xylopyranoside (6894-01-5) → 9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N2-(methoxyacetyl)-N6-isobutyryl-9H-purine-2,6-diamine 2'(2-cyanoethyl diisopropylphosphoramidite) (457880-66-9)

Guidance literature:

Multi-step reaction with 12 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 / acetonitrile / 0.33 h / 60 °C

6.2: Et₃SiOTf / acetonitrile / 0.83 h / 45 °C

7.1: 6.33 g / Et₄NF*2H₂O; AcOH / acetonitrile / 3.5 h / 25 °C

8.1: sym-collidine; AgNO₃ / CH₂Cl₂ / 0.5 h / 25 °C

9.1: NaN₃ / pyridine / 3 h / 65 °C

9.2: PPh₃ / pyridine / 0.75 h / 25 °C

9.3: 8.29 g / Et₃N*AcOH / methanol; tetrahydrofuran / 65 °C

10.1: DMAP / CH₂Cl₂; pyridine / 1 h / 25 °C

11.1: 6.7 g / NaOH; water / tetrahydrofuran; ethanol / 0.08 h / 4 °C

12.1: 90 percent / iPr₂NEt / CH₂Cl₂ / 4 h / 25 °C

With pyridine; 2,4,6-trimethyl-pyridine; dmap; sodium hydroxide; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; water; hydrogen; sodium methylate; tetraethylammonium fluoride; silver nitrate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; 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) → 9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N2-(methoxyacetyl)-N6-isobutyryl-9H-purine-2,6-diamine 2'(2-cyanoethyl diisopropylphosphoramidite) (457880-66-9)

Guidance literature:

Multi-step reaction with 10 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 / acetonitrile / 0.33 h / 60 °C

4.2: Et₃SiOTf / acetonitrile / 0.83 h / 45 °C

5.1: 6.33 g / Et₄NF*2H₂O; AcOH / acetonitrile / 3.5 h / 25 °C

6.1: sym-collidine; AgNO₃ / CH₂Cl₂ / 0.5 h / 25 °C

7.1: NaN₃ / pyridine / 3 h / 65 °C

7.2: PPh₃ / pyridine / 0.75 h / 25 °C

7.3: 8.29 g / Et₃N*AcOH / methanol; tetrahydrofuran / 65 °C

8.1: DMAP / CH₂Cl₂; pyridine / 1 h / 25 °C

9.1: 6.7 g / NaOH; water / tetrahydrofuran; ethanol / 0.08 h / 4 °C

10.1: 90 percent / iPr₂NEt / CH₂Cl₂ / 4 h / 25 °C

With pyridine; 2,4,6-trimethyl-pyridine; dmap; sodium hydroxide; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; water; hydrogen; tetraethylammonium fluoride; silver nitrate; acetic acid; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; pyridine; ethanol; dichloromethane; acetonitrile;

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

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]-N⁶-isobutyryl-N²-(methoxyacetyl)-9H-purine-2,6-diamine

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

4,4'-dimethoxytrityl chloride

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