2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine

Base Information

Chemical Name:2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine
CAS No.:268748-04-5
Molecular Formula:C₃₉H₄₇N₅O₇Si
Molecular Weight:725.917
Hs Code.:

Synonyms:2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine

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Chemical Property of 2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine

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Technology Process of 2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine

There total 11 articles about 2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 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:

: 103931-45-9
5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

: 268748-04-5
2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine

Guidance literature:: Multi-step reaction with 8 steps

1.1: CH₂Cl₂ / 20 °C

2.1: Bu₄NF / tetrahydrofuran / 5 h / 4 °C

3.1: 43 percent / NaBH₄ / ethanol

4.1: 97 percent / pyridine

5.1: 25 percent / H₂SO₄ / acetic acid / 3 h

6.1: 75 percent / SnCl₄ / acetonitrile / 24 h

7.1: NaOH / methanol; H₂O / 20 °C

7.2: Et₃N / pyridine / 24 h / 20 °C

8.1: NaOH / methanol; H₂O

8.2: imidazole / CH₂Cl₂; dimethylformamide / 72 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; sulfuric acid; tetrabutyl ammonium fluoride; tin(IV) chloride; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetic acid; acetonitrile; 1.1: Substitution / 2.1: desilylation / 3.1: Hydrogenation / 4.1: Acetylation / 5.1: Acetylation / 6.1: Substitution / 7.1: Hydrolysis / 7.2: tritylation; lactonization / 8.1: Ring cleavage / 8.2: silylation;
DOI:10.1021/jo991399g

Reference yield:

: 279248-77-0
3-deoxy-3-[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-α-D-erythro-pentofuranose

: 268748-04-5
2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 43 percent / NaBH₄ / ethanol

2.1: 97 percent / pyridine

3.1: 25 percent / H₂SO₄ / acetic acid / 3 h

4.1: 75 percent / SnCl₄ / acetonitrile / 24 h

5.1: NaOH / methanol; H₂O / 20 °C

5.2: Et₃N / pyridine / 24 h / 20 °C

6.1: NaOH / methanol; H₂O

6.2: imidazole / CH₂Cl₂; dimethylformamide / 72 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; sulfuric acid; tin(IV) chloride; In pyridine; methanol; ethanol; water; acetic acid; acetonitrile; 1.1: Hydrogenation / 2.1: Acetylation / 3.1: Acetylation / 4.1: Substitution / 5.1: Hydrolysis / 5.2: tritylation; lactonization / 6.1: Ring cleavage / 6.2: silylation;
DOI:10.1021/jo991399g

Reference yield:

: 279248-76-9
5-O-(tert-butyldimethylsilyl)-3-deoxy-3-[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-α-D-erythro-pentofuranose

: 268748-04-5
2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine

Guidance literature:: Multi-step reaction with 7 steps

1.1: Bu₄NF / tetrahydrofuran / 5 h / 4 °C

2.1: 43 percent / NaBH₄ / ethanol

3.1: 97 percent / pyridine

4.1: 25 percent / H₂SO₄ / acetic acid / 3 h

5.1: 75 percent / SnCl₄ / acetonitrile / 24 h

6.1: NaOH / methanol; H₂O / 20 °C

6.2: Et₃N / pyridine / 24 h / 20 °C

7.1: NaOH / methanol; H₂O

7.2: imidazole / CH₂Cl₂; dimethylformamide / 72 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; sulfuric acid; tetrabutyl ammonium fluoride; tin(IV) chloride; In tetrahydrofuran; pyridine; methanol; ethanol; water; acetic acid; acetonitrile; 1.1: desilylation / 2.1: Hydrogenation / 3.1: Acetylation / 4.1: Acetylation / 5.1: Substitution / 6.1: Hydrolysis / 6.2: tritylation; lactonization / 7.1: Ring cleavage / 7.2: silylation;
DOI:10.1021/jo991399g