Toluene-4-sulfonic acid (4R,5S)-6-azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (4R,5S)-6-azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexyl ester
• CAS No.: 452084-59-2
• Molecular Formula: C₂₆H₃₉N₃O₅SSi
• Molecular Weight: 533.764
• Mol file: 452084-59-2.mol

Synonyms:Toluene-4-sulfonic acid (4R,5S)-6-azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexyl ester

Chemical Property of Toluene-4-sulfonic acid (4R,5S)-6-azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (4R,5S)-6-azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexyl ester

There total 13 articles about Toluene-4-sulfonic acid (4R,5S)-6-azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexyl 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: 91.0%

p-toluenesulfonyl chloride (98-59-9) + (4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol (452084-67-2) → Toluene-4-sulfonic acid (4R,5S)-6-azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexyl ester (452084-59-2)

Guidance literature:

With TEA; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(02)00681-0

Reference yield:

benzyl bromide (100-39-0) → Toluene-4-sulfonic acid (4R,5S)-6-azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexyl ester (452084-59-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / NaH / tetrahydrofuran / 20 °C

2: 79 percent / BH₃-DMS; H₂O₂ / tetrahydrofuran / 0 °C

3: 89 percent / NaH / tetrahydrofuran / 20 °C

4: 93 percent / TFA / tetrahydrofuran; H₂O / 20 °C

5: TEA / CH₂Cl₂ / 0 - 20 °C

6: K₂CO₃ / methanol / 20 °C

7: 97 percent / NaN₃; NH₄Cl / dimethylformamide / 100 °C

8: 75 percent / imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

9: 95 percent / DDQ / CH₂Cl₂; H₂O / 20 °C

10: 91 percent / TEA / CH₂Cl₂ / 0 °C

With 1H-imidazole; dmap; sodium azide; dimethylsulfide borane complex; TEA; dihydrogen peroxide; sodium hydride; potassium carbonate; ammonium chloride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)00681-0

Reference yield:

6-(4-methoxybenzyloxy)hex-1-en-3-ol (154476-70-7) → Toluene-4-sulfonic acid (4R,5S)-6-azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexyl ester (452084-59-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 40 percent / tert-butyl-hydroperoxide; TTIP; (-)-DIPT / CH₂Cl₂ / -20 °C

2: 94 percent / NaH; Bu₄NI / tetrahydrofuran / 20 °C

3: 97 percent / NaN₃; NH₄Cl / dimethylformamide / 100 °C

4: 75 percent / imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

5: 95 percent / DDQ / CH₂Cl₂; H₂O / 20 °C

6: 91 percent / TEA / CH₂Cl₂ / 0 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium azide; TEA; tetra-(n-butyl)ammonium iodide; sodium hydride; D-(-)-diisopropyl tartrate; ammonium chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4039(02)00681-0

upstream raw materials:

p-toluenesulfonyl chloride

(4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol

benzyl bromide

6-(4-methoxybenzyloxy)hex-1-en-3-ol

Downstream raw materials:

1,1-dimethylethyl (3R)-trans-hexahydro-4-hydroxy-3-{[4-(phenylmethoxy)benzoyl]amino}-1H-azepine-1-carboxylate

tert-butyl (3R,4R)-3-azido-4-(benzyloxy)azepane-1-carboxylate

tert-butyl (3S,4R)-4-(benzyloxy)-3-hydroxyazepane-1-carboxylate

tert-butyl (3S,4R)-4-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)azepane-1-carboxylate

Refernces