(2R,3S,4R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophene-2-carboxylic acid methylamide

Base Information

• Chemical Name: (2R,3S,4R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophene-2-carboxylic acid methylamide
• CAS No.: 911701-36-5
• Molecular Formula: C₂₈H₃₄ClIN₆O₅S
• Molecular Weight: 729.039
• Mol file: 911701-36-5.mol

Synonyms:(2R,3S,4R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophene-2-carboxylic acid methylamide

Chemical Property of (2R,3S,4R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophene-2-carboxylic acid methylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophene-2-carboxylic acid methylamide

There total 6 articles about (2R,3S,4R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophene-2-carboxylic acid methylamide 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: 52.0%

(2R,3S,4R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophene-2-carboxylic acid methyl ester + methylamine (74-89-5) → (2R,3S,4R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophene-2-carboxylic acid methylamide (911701-36-5)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ol061548z

Reference yield:

(1S,2S,3R)-2,6-dichloro-9-(2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl)-9H-purine (911701-28-5) → (2R,3S,4R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophene-2-carboxylic acid methylamide (911701-36-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 88 percent / hydrochloric acid / H₂O; tetrahydrofuran / 6 h / 20 °C

2.1: 93 percent / PPTS / CH₂Cl₂ / 12 h / 20 °C

3.1: LiHMDS / tetrahydrofuran / 1.5 h / -78 °C

3.2: 78 percent / tetrahydrofuran / 2 h / -78 °C

4.1: 82 percent / tetrahydrofuran; ethanol

5.1: 52 percent / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; pyridinium p-toluenesulfonate; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1021/ol061548z

Reference yield:

(1S,2S,3R)-(2,6-dichloro-purin-9-yl)-tetrahydro-thiophene-3,4-diol (911701-31-0) → (2R,3S,4R)-2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3,4-bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophene-2-carboxylic acid methylamide (911701-36-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / PPTS / CH₂Cl₂ / 12 h / 20 °C

2.1: LiHMDS / tetrahydrofuran / 1.5 h / -78 °C

2.2: 78 percent / tetrahydrofuran / 2 h / -78 °C

3.1: 82 percent / tetrahydrofuran; ethanol

4.1: 52 percent / tetrahydrofuran / 2 h / 20 °C

With pyridinium p-toluenesulfonate; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ol061548z

upstream raw materials:

methylamine

(1S,2S,3R)-(2,6-dichloro-purin-9-yl)-tetrahydro-thiophene-3,4-diol

(1S,2S,3R)-2,6-dichloro-9-(2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl)-9H-purine

9-[(2S,3S,4R)-3,4-Bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophen-2-yl]-2,6-dichloro-9H-purine