benzoic acid (2R,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-3,4-dihydroxy-tetrahydro-thiophen-2-yl methyl ester

Base Information

• Chemical Name: benzoic acid (2R,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-3,4-dihydroxy-tetrahydro-thiophen-2-yl methyl ester
• CAS No.: 666750-34-1
• Molecular Formula: C₂₄H₂₁ClIN₅O₄S
• Molecular Weight: 637.885
• Mol file: 666750-34-1.mol

Synonyms:benzoic acid (2R,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-3,4-dihydroxy-tetrahydro-thiophen-2-yl methyl ester

Chemical Property of benzoic acid (2R,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-3,4-dihydroxy-tetrahydro-thiophen-2-yl methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoic acid (2R,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-3,4-dihydroxy-tetrahydro-thiophen-2-yl methyl ester

There total 14 articles about benzoic acid (2R,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-3,4-dihydroxy-tetrahydro-thiophen-2-yl methyl ester 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: 99.0%

benzoic acid (3aS,4R,6R,6aR)-6-(2-chloro-6-(3-iodo-benzylamino)-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester (596103-11-6) → 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)

Guidance literature:

With acetic acid; at 70 ℃; for 12h;

DOI:10.1021/jm034098e

Reference yield:

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 (596103-10-5) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. acetic acid

With acetic acid;

DOI:10.1081/NCN-200061827

Reference yield:

2,3:5,6-di-O-isopropylidene-D-gulitol (3969-61-7,20581-94-6,71771-89-6,73209-94-6,109008-02-8,120442-06-0,127707-49-7,28910-18-1) → 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)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 98 percent / pyridine / 4 h / 0 °C

2.1: 94 percent / Na₂S*H₂O / dimethylformamide / 3 h / 100 °C

3.1: 43 percent / aq. AcOH / 4 h / 20 °C

4.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h

5.1: 98 percent / NaBH₄ / methanol / 0.5 h / 0 °C

6.1: 99 percent / pyridine / 6 h / 20 °C

7.1: 95 percent / m-CPBA / CH₂Cl₂ / 0.75 h / -78 °C

8.1: Et₃N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C

8.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C

9.1: 90 percent / Et₃N / ethanol / 24 h / 20 °C

10.1: aq. AcOH / 12 h / 70 °C

With pyridine; lead(IV) acetate; sodium sulfide; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm050595e

upstream raw materials:

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

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

2,3:5,6-di-O-isopropylidene-D-gulitol

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

{(2R,3S,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodobenzylamino)-purin-9-yl]-tetrahydro-thiophen-2-yl}-methanol

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

(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