1,1-dimethylethyl 6(S)-azido-5,6,7,8,9-pentadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-1,2,3-tri-O-acetyl-β-D-ribo-decofuranuronate

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Chemical Name:1,1-dimethylethyl 6(S)-azido-5,6,7,8,9-pentadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-1,2,3-tri-O-acetyl-β-D-ribo-decofuranuronate
CAS No.:124289-01-6
Molecular Formula:C₂₇H₃₈N₄O₁₁S
Molecular Weight:626.685
Hs Code.:

Synonyms:1,1-dimethylethyl 6(S)-azido-5,6,7,8,9-pentadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-1,2,3-tri-O-acetyl-β-D-ribo-decofuranuronate

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Chemical Property of 1,1-dimethylethyl 6(S)-azido-5,6,7,8,9-pentadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-1,2,3-tri-O-acetyl-β-D-ribo-decofuranuronate

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Technology Process of 1,1-dimethylethyl 6(S)-azido-5,6,7,8,9-pentadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-1,2,3-tri-O-acetyl-β-D-ribo-decofuranuronate

There total 13 articles about 1,1-dimethylethyl 6(S)-azido-5,6,7,8,9-pentadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-1,2,3-tri-O-acetyl-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:

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

: 124289-01-6
1,1-dimethylethyl 6(S)-azido-5,6,7,8,9-pentadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-1,2,3-tri-O-acetyl-β-D-ribo-decofuranuronate

Guidance literature:: Multi-step reaction with 12 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

With pyridine; hydrogenchloride; potassium fluoride; sodium azide; ammonium cerium(IV) nitrate; ammonium chloride; hydrogen; nitric acid; sodium acetate; L-Selectride; 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

: 124289-01-6
1,1-dimethylethyl 6(S)-azido-5,6,7,8,9-pentadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-1,2,3-tri-O-acetyl-β-D-ribo-decofuranuronate

Guidance literature:: Multi-step reaction with 11 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

With pyridine; hydrogenchloride; potassium fluoride; sodium azide; ammonium cerium(IV) nitrate; ammonium chloride; hydrogen; nitric acid; sodium acetate; L-Selectride; 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

Reference yield:

: 33985-40-9
(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

: 124289-01-6
1,1-dimethylethyl 6(S)-azido-5,6,7,8,9-pentadeoxy-9(S)-<<(4-methylphenyl)sulfonyl>amino>-1,2,3-tri-O-acetyl-β-D-ribo-decofuranuronate

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / KF / acetonitrile / 24 h / 22 °C

2: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C

3: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C

4: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 °C

5: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

6: pyridine / 1 h / 0 °C

7: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 °C

8: 4 N HCl / dioxane / 96 h / 22 °C

9: 554 mg / sodium acetate / 6.5 h / 50 °C

With pyridine; hydrogenchloride; potassium fluoride; sodium azide; ammonium cerium(IV) nitrate; ammonium chloride; nitric acid; sodium acetate; L-Selectride; acetic acid; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; In tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00290a028