Benzoic acid (2R,3S,4S,5R)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-fluoro-5-methylcarbamoyl-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,4S,5R)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-fluoro-5-methylcarbamoyl-tetrahydro-furan-3-yl ester
CAS No.:551929-68-1
Molecular Formula:C₂₅H₂₁ClFIN₆O₄
Molecular Weight:650.835
Hs Code.:

Synonyms:Benzoic acid (2R,3S,4S,5R)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-fluoro-5-methylcarbamoyl-tetrahydro-furan-3-yl ester

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Chemical Property of Benzoic acid (2R,3S,4S,5R)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-fluoro-5-methylcarbamoyl-tetrahydro-furan-3-yl ester

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Technology Process of Benzoic acid (2R,3S,4S,5R)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-fluoro-5-methylcarbamoyl-tetrahydro-furan-3-yl ester

There total 16 articles about Benzoic acid (2R,3S,4S,5R)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-fluoro-5-methylcarbamoyl-tetrahydro-furan-3-yl 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: 35.0%

: 74-89-5
methylamine

: 551929-66-9
(2R,3S,4S,5R)-4-Benzoyloxy-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-fluoro-tetrahydro-furan-2-carboxylic acid methyl ester

: (4R,5R)-5-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-hydroxy-4,5-dihydro-furan-2-carboxylic acid methylamide

: (2R,3S,4S,5R)-5-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-fluoro-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide

: 551929-68-1
Benzoic acid (2R,3S,4S,5R)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-fluoro-5-methylcarbamoyl-tetrahydro-furan-3-yl ester

Guidance literature:: In tetrahydrofuran; at 20 ℃; for 0.0666667h;
DOI:10.1016/S0960-894X(03)00027-1

Reference yield:

: 152711-00-7
Methyl 3-deoxy-3-fluoro-β-D-arabinofuranoside

: 551929-68-1
Benzoic acid (2R,3S,4S,5R)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-fluoro-5-methylcarbamoyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 12 steps

1: pyridine

2: 52 percent / 18-crown-6 / dimethylsulfoxide / Heating

3: MeONa

4: RuCl₃; NaIO₄ / acetonitrile; CCl₄; H₂O

5: DCC; DMAP

6: TBAF; AcOH / tetrahydrofuran

7: 83 percent / AcOH; H₂SO₄

8: 91 percent / TMSOTf

With pyridine; dmap; ruthenium trichloride; sodium periodate; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; tetrachloromethane; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1081/NCN-120022701

Reference yield:

: 237410-10-5
((2R,3S,4S,5R)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate

: 551929-68-1
Benzoic acid (2R,3S,4S,5R)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-fluoro-5-methylcarbamoyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: MeONa

2: RuCl₃; NaIO₄ / acetonitrile; CCl₄; H₂O

3: DCC; DMAP

4: TBAF; AcOH / tetrahydrofuran

5: 83 percent / AcOH; H₂SO₄

6: 91 percent / TMSOTf

With dmap; ruthenium trichloride; sodium periodate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;
DOI:10.1081/NCN-120022701