(2S,5S)-5-Azido-6-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester

Base Information

• Chemical Name: (2S,5S)-5-Azido-6-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester
• CAS No.: 124288-89-7
• Molecular Formula: C₃₇H₄₃N₉O₁₀S
• Molecular Weight: 805.869
• Mol file: 124288-89-7.mol

Synonyms:

Chemical Property of (2S,5S)-5-Azido-6-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-5-Azido-6-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester

There total 14 articles about (2S,5S)-5-Azido-6-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl 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: 50.0%

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 (124289-01-6) + N-Benzoyl-N,9-bis(trimethylsilyl)adenin (18055-47-5) → (2S,5S)-5-Azido-6-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester (124288-89-7)

Guidance literature:

tin(IV) chloride;

DOI:10.1021/jo00290a028

Reference yield:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → (2S,5S)-5-Azido-6-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester (124288-89-7)

Guidance literature:

Multi-step reaction with 10 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

10: 50 percent / SnCl₄

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; tin(IV) chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00290a028

Reference yield:

1,1-dimethylethyl (S)-5-amino-2-<<(4-methylphenyl)sulfonyl>-amino>pentanoate (124288-74-0) → (2S,5S)-5-Azido-6-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester (124288-89-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 56 percent / m-CPBA / CH₂Cl₂ / 0.28 h / Heating

2: 86 percent / KF / acetonitrile / 24 h / 22 °C

3: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C

4: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C

5: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 °C

6: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

7: pyridine / 1 h / 0 °C

8: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 °C

9: 4 N HCl / dioxane / 96 h / 22 °C

10: 554 mg / sodium acetate / 6.5 h / 50 °C

11: 50 percent / SnCl₄

With pyridine; hydrogenchloride; potassium fluoride; sodium azide; ammonium cerium(IV) nitrate; ammonium chloride; nitric acid; sodium acetate; L-Selectride; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; tin(IV) chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00290a028

upstream raw materials:

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

N-Benzoyl-N,9-bis(trimethylsilyl)adenin

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

1,1-dimethylethyl (S)-5-amino-2-<<(4-methylphenyl)sulfonyl>-amino>pentanoate