(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide

Base Information

Chemical Name:(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide
CAS No.:786666-17-9
Molecular Formula:C₂₅H₃₄ClIN₈O₄Si
Molecular Weight:701.039
Hs Code.:

(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide

Synonyms:(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide

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Chemical Property of (2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide

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Technology Process of (2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide

There total 14 articles about (2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-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: 71.0%

: 786666-13-5
(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[3-(2-chloro-acetyl)-ureido]-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid methylamide

: 786666-17-9
(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 18h;
DOI:10.1016/j.bmcl.2004.07.042

Reference yield:

: 35085-25-7
3-azido-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

: 786666-17-9
(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide

Guidance literature:: Multi-step reaction with 12 steps

1: aq. NaIO₄; RuCl₃ / CCl₄; acetonitrile / 4 h / 20 °C

2: (COCl)2; DMF / CH₂Cl₂ / 16 h / 20 °C

3: CH₂Cl₂ / 3 h / 0 °C

4: aq. formic acid / 1.5 h / 60 °C

5: pyridine / 16 h / 20 °C

6: 50 percent / TMSOTf / 1,2-dichloro-ethane / 2 h / 0 - 60 °C

7: Et₃N / ethanol / 18 h / 50 °C

8: NaOMe / methanol / 2 h / 20 °C

9: 69 percent / imidazole / dimethylformamide / 24 h / 20 °C

10: 90 percent / Ph₃P; aq. NH₃ / tetrahydrofuran / 18 h / 20 °C

11: 86 percent / dimethylformamide / 3 h / 0 °C

12: 71 percent / NaOMe / methanol / 18 h / 20 °C

With pyridine; 1H-imidazole; ruthenium trichloride; ammonium hydroxide; sodium periodate; formic acid; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sodium methylate; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmcl.2004.07.042

Reference yield:

: 21870-78-0
3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 786666-17-9
(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-ureido-tetrahydro-furan-2-carboxylic acid methylamide

Guidance literature:: Multi-step reaction with 13 steps

1: aq. AcOH / 1.5 h / 55 °C

2: aq. NaIO₄; RuCl₃ / CCl₄; acetonitrile / 4 h / 20 °C

3: (COCl)2; DMF / CH₂Cl₂ / 16 h / 20 °C

4: CH₂Cl₂ / 3 h / 0 °C

5: aq. formic acid / 1.5 h / 60 °C

6: pyridine / 16 h / 20 °C

7: 50 percent / TMSOTf / 1,2-dichloro-ethane / 2 h / 0 - 60 °C

8: Et₃N / ethanol / 18 h / 50 °C

9: NaOMe / methanol / 2 h / 20 °C

10: 69 percent / imidazole / dimethylformamide / 24 h / 20 °C

11: 90 percent / Ph₃P; aq. NH₃ / tetrahydrofuran / 18 h / 20 °C

12: 86 percent / dimethylformamide / 3 h / 0 °C

13: 71 percent / NaOMe / methanol / 18 h / 20 °C

With pyridine; 1H-imidazole; ruthenium trichloride; ammonium hydroxide; sodium periodate; formic acid; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sodium methylate; acetic acid; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmcl.2004.07.042