(2S,3S,4R)-N-[(R)-2-acetoxytetracosanoyl]-2-amino-3,4-di-O-benzoyl-1-O-(tert-butyl(diphenyl)silyl)-16-methylheptadecane-1,3,4-triol

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Chemical Name:(2S,3S,4R)-N-[(R)-2-acetoxytetracosanoyl]-2-amino-3,4-di-O-benzoyl-1-O-(tert-butyl(diphenyl)silyl)-16-methylheptadecane-1,3,4-triol
CAS No.:911371-66-9
Molecular Formula:C₇₄H₁₁₃NO₈Si
Molecular Weight:1172.8
Hs Code.:

Synonyms:(2S,3S,4R)-N-[(R)-2-acetoxytetracosanoyl]-2-amino-3,4-di-O-benzoyl-1-O-(tert-butyl(diphenyl)silyl)-16-methylheptadecane-1,3,4-triol

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Chemical Property of (2S,3S,4R)-N-[(R)-2-acetoxytetracosanoyl]-2-amino-3,4-di-O-benzoyl-1-O-(tert-butyl(diphenyl)silyl)-16-methylheptadecane-1,3,4-triol

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Technology Process of (2S,3S,4R)-N-[(R)-2-acetoxytetracosanoyl]-2-amino-3,4-di-O-benzoyl-1-O-(tert-butyl(diphenyl)silyl)-16-methylheptadecane-1,3,4-triol

There total 9 articles about (2S,3S,4R)-N-[(R)-2-acetoxytetracosanoyl]-2-amino-3,4-di-O-benzoyl-1-O-(tert-butyl(diphenyl)silyl)-16-methylheptadecane-1,3,4-triol 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: 95.0%

: 911371-63-6
(2S,3S,4R)-2-amino-3,4-di-O-benzoyl-1-O-(tert-butyl(diphenyl)silyl)-16-methylheptadecane-1,3,4-triol

: 127061-75-0
(R)-2-Acetoxytetracosanoic acid

: 911371-66-9
(2S,3S,4R)-N-[(R)-2-acetoxytetracosanoyl]-2-amino-3,4-di-O-benzoyl-1-O-(tert-butyl(diphenyl)silyl)-16-methylheptadecane-1,3,4-triol

Guidance literature:: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ol061444o

Reference yield:

: 911371-53-4
(4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(R)-ethan-1-ol

: 911371-66-9
(2S,3S,4R)-N-[(R)-2-acetoxytetracosanoyl]-2-amino-3,4-di-O-benzoyl-1-O-(tert-butyl(diphenyl)silyl)-16-methylheptadecane-1,3,4-triol

Guidance literature:: Multi-step reaction with 8 steps

1: 76 percent / generation II Grubbs catalyst / CH₂Cl₂ / 24 h / Heating

2: 94 percent / H₂ / Pd(OH)2 / ethyl acetate / 1.5 h / 20 °C

3: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 12 h / 0 °C

4: 122 mg / tetramethylguanidinium azide / dimethylformamide / 0.17 h / 0 °C

5: 92 percent / trifluoroacetic acid / H₂O; CH₂Cl₂ / 0.5 h / 20 °C

6: 89 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

7: 95 percent / H₂ / Pd(OH)2 / methanol; ethyl acetate / 4 h / 20 °C

8: 95 percent / 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; generation II Grubbs catalyst; hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; tetramethylguanidinum azide; trifluoroacetic acid; palladium dihydroxide; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol061444o

Reference yield:

: 911371-57-8
(2R,3S,4R)-1-O-(tert-butyl(diphenyl)silyl)-3,4-O-isopropylidene-16-methylheptadecane-1,2,3,4-tetrol

: 911371-66-9
(2S,3S,4R)-N-[(R)-2-acetoxytetracosanoyl]-2-amino-3,4-di-O-benzoyl-1-O-(tert-butyl(diphenyl)silyl)-16-methylheptadecane-1,3,4-triol

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 12 h / 0 °C

2: 122 mg / tetramethylguanidinium azide / dimethylformamide / 0.17 h / 0 °C

3: 92 percent / trifluoroacetic acid / H₂O; CH₂Cl₂ / 0.5 h / 20 °C

4: 89 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

5: 95 percent / H₂ / Pd(OH)2 / methanol; ethyl acetate / 4 h / 20 °C

6: 95 percent / 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; tetramethylguanidinum azide; trifluoroacetic acid; palladium dihydroxide; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol061444o