1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate

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Chemical Name:1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate
CAS No.:124288-91-1
Molecular Formula:C₂₆H₃₅N₉O₇S
Molecular Weight:617.686
Hs Code.:

Synonyms:1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate

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Chemical Property of 1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate

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Technology Process of 1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate

There total 15 articles about 1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate 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: 88.0%

: 124288-90-0
1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-2,3-di-O-acetyl-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate

: 124288-91-1
1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate

Guidance literature:: With potassium carbonate; acetic acid; In methanol; at 22 ℃; for 0.75h;
DOI:10.1021/jo00290a028

Reference yield:

: 110414-90-9
α-N-tosyl-δ-N-carbobenzoxyornthine

: 124288-91-1
1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate

Guidance literature:: Multi-step reaction with 14 steps

1: 82 percent / CHCl₃ / 22 h / 22 °C

2: 99 percent / H₂ / 10percent Pd/C / methanol / 3102.9 Torr

3: 56 percent / m-CPBA / CH₂Cl₂ / 0.28 h / Heating

4: 86 percent / KF / acetonitrile / 24 h / 22 °C

5: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C

6: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C

7: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 °C

8: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

9: pyridine / 1 h / 0 °C

10: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 °C

11: 4 N HCl / dioxane / 96 h / 22 °C

12: 554 mg / sodium acetate / 6.5 h / 50 °C

13: 59 percent / SnCl₄ / CH₂Cl₂; acetonitrile / 16 h / 22 °C

14: 88 percent / potassium carbonate, acetic acid / methanol / 0.75 h / 22 °C

With pyridine; hydrogenchloride; potassium fluoride; sodium azide; ammonium cerium(IV) nitrate; ammonium chloride; hydrogen; nitric acid; sodium acetate; tin(IV) chloride; L-Selectride; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00290a028

Reference yield:

: 124288-73-9
1,1-dimethylethyl (S)-2-<<(4-methylphenyl)sulfonyl>-amino>-5-<<(phenylmethoxy)carbonyl>amino>pentanoate

: 124288-91-1
1,1-dimethylethyl 1-(6-amino-9H-purin-9yl)-6(S)-azido-1,5,6,7,8,9-hexadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-β-D-ribo-decofuranuronate

Guidance literature:: Multi-step reaction with 13 steps

1: 99 percent / H₂ / 10percent Pd/C / methanol / 3102.9 Torr

2: 56 percent / m-CPBA / CH₂Cl₂ / 0.28 h / Heating

3: 86 percent / KF / acetonitrile / 24 h / 22 °C

4: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C

5: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C

6: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 °C

7: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

8: pyridine / 1 h / 0 °C

9: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 °C

10: 4 N HCl / dioxane / 96 h / 22 °C

11: 554 mg / sodium acetate / 6.5 h / 50 °C

12: 59 percent / SnCl₄ / CH₂Cl₂; acetonitrile / 16 h / 22 °C

13: 88 percent / potassium carbonate, acetic acid / methanol / 0.75 h / 22 °C

With pyridine; hydrogenchloride; potassium fluoride; sodium azide; ammonium cerium(IV) nitrate; ammonium chloride; hydrogen; nitric acid; sodium acetate; tin(IV) chloride; L-Selectride; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00290a028