(2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid

Base Information

• Chemical Name: (2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid
• CAS No.: 378238-87-0
• Molecular Formula: C₂₁H₁₇N₅O₈
• Molecular Weight: 467.395
• Mol file: 378238-87-0.mol

Synonyms:(2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid

Chemical Property of (2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid

There total 13 articles about (2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid 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: 58.0%

N6-benzoyladenine (378238-86-9) → (2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid (378238-87-0)

Guidance literature:

With lithium hydroxide; In ethanol; water; for 1.5h;

DOI:10.1021/ol0167210

Reference yield:

N-benzoyladenine (4005-49-6) → (2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid (378238-87-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / 80 °C

1.2: 75 percent / Me₃SiOTf / acetonitrile / 1.5 h / 80 °C

2.1: 90 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 61 percent / N-benzoyladenine / diphenyl ether / 0.03 h / Heating

4.1: 58 percent / LiOH / ethanol; H₂O / 1.5 h

With lithium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; N-benzoyladenine; In diphenylether; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1021/ol0167210

Reference yield:

(3aR,6S,6aR)-5-[1-Iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (378238-91-6) → (2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid (378238-87-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LiN(SiMe₃)2 / diethyl ether / 0.25 h / -78 °C

1.2: 86 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

2.1: 33 percent / n-Bu₃SnH; AIBN / benzene / 6 h / 80 °C

3.1: 30 percent / AIBN; NaHCO₃ / CHCl₃ / 36 h / Heating

4.1: H₂SO₄ / acetic acid; CH₂Cl₂ / 7 h / 20 °C

5.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / 80 °C

5.2: 75 percent / Me₃SiOTf / acetonitrile / 1.5 h / 80 °C

6.1: 90 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 61 percent / N-benzoyladenine / diphenyl ether / 0.03 h / Heating

8.1: 58 percent / LiOH / ethanol; H₂O / 1.5 h

With lithium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; N-benzoyladenine; lithium hexamethyldisilazane; In diphenylether; diethyl ether; ethanol; dichloromethane; chloroform; water; acetic acid; acetonitrile; benzene;

DOI:10.1021/ol0167210

upstream raw materials:

N⁶-benzoyladenine

N-benzoyladenine

(3aR,6S,6aR)-5-[1-Iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

(3aR,3bS,5R,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-3a,3b,5,7a-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester