(2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2-chloro-6-(3-iodobenzylamino)purin-9-yl)-tetrahydro-thiophene-2-carboxylic acid methylamide

Base Information

• Chemical Name: (2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2-chloro-6-(3-iodobenzylamino)purin-9-yl)-tetrahydro-thiophene-2-carboxylic acid methylamide
• CAS No.: 666830-47-3
• Molecular Formula: C₃₀H₄₆ClIN₆O₃SSi₂
• Molecular Weight: 789.328
• Mol file: 666830-47-3.mol

Synonyms:(2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2-chloro-6-(3-iodobenzylamino)purin-9-yl)-tetrahydro-thiophene-2-carboxylic acid methylamide

Chemical Property of (2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2-chloro-6-(3-iodobenzylamino)purin-9-yl)-tetrahydro-thiophene-2-carboxylic acid methylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2-chloro-6-(3-iodobenzylamino)purin-9-yl)-tetrahydro-thiophene-2-carboxylic acid methylamide

There total 19 articles about (2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2-chloro-6-(3-iodobenzylamino)purin-9-yl)-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: 42.0%

methylamine (74-89-5) + (2S,3S,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-thiophene-2-carboxylic acid methyl ester → (2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2-chloro-6-(3-iodobenzylamino)purin-9-yl)-tetrahydro-thiophene-2-carboxylic acid methylamide (666830-47-3)

Guidance literature:

In tetrahydrofuran; at 50 ℃; for 24h; Product distribution / selectivity;

Reference yield:

methylamine (74-89-5) + (2S,3S,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-thiophene-2-carboxylic acid (871913-94-9) → (2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2-chloro-6-(3-iodobenzylamino)purin-9-yl)-tetrahydro-thiophene-2-carboxylic acid methylamide (666830-47-3)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/jm050595e

Reference yield:

benzoic acid (2R,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-3,4-dihydroxy-tetrahydro-thiophen-2-yl methyl ester (666750-34-1) → (2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2-chloro-6-(3-iodobenzylamino)purin-9-yl)-tetrahydro-thiophene-2-carboxylic acid methylamide (666830-47-3)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethylformamide

2: NaOMe / methanol

3: PDC / dimethylformamide

4: K₂CO₃

5: methanol

With dipyridinium dichromate; sodium methylate; potassium carbonate; In methanol; N,N-dimethyl-formamide;

DOI:10.1081/NCN-200061827

upstream raw materials:

methylamine

(2S,3S,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-thiophene-2-carboxylic acid

3-iodobenzylamine

benzoic acid (3aS,4R,6R,6aR)-6-(2,6-dichloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

Downstream raw materials:

(2S,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-thiophene-2-carboxylic acid methylamide