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

Base Information

Chemical Name:3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 2',3'-lactone
CAS No.:279248-94-1
Molecular Formula:C₃₃H₃₁N₅O₆
Molecular Weight:593.639
Hs Code.:

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

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

Chemical Property:

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

There total 9 articles about 3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 2',3'-lactone 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

: 279248-94-1
3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 2',3'-lactone

Guidance literature:: Multi-step reaction with 7 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

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;
DOI:10.1021/jo991399g

Reference yield:

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

: 279248-94-1
3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 2',3'-lactone

Guidance literature:: Multi-step reaction with 5 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

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;
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

: 279248-94-1
3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 2',3'-lactone

Guidance literature:: Multi-step reaction with 6 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

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;
DOI:10.1021/jo991399g