(3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid

Base Information

Chemical Name:(3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid
CAS No.:752251-16-4
Molecular Formula:C₃₉H₆₇NO₇Si₃
Molecular Weight:746.22
Hs Code.:

Synonyms:(3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid

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Chemical Property of (3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid

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Technology Process of (3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid

There total 12 articles about (3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid 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:

: 752251-15-3
(3R,5R,6S)-6-(2-benzyloxy-benzoylamino)-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)heptanoic acid methyl ester

: 752251-16-4
(3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid

Guidance literature:: With sodium hydroxide; In methanol; at 0 - 20 ℃;
DOI:10.1002/anie.200453909

Reference yield:

: 752251-08-4
(4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-oxo-pentanoic acid methyl ester

: 752251-16-4
(3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: 48 percent / NaBH₄ / methanol; diethyl ether / 6 h / -60 °C

2.1: 78 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

3.1: 54 percent / aq. NaOH / tetrahydrofuran; methanol / 4 h / 0 - 20 °C

4.1: tetrahydrofuran / 1 h / 0 °C

5.1: MgCl₂ / tetrahydrofuran / 5 h / Heating

5.2: 3.38 g / tetrahydrofuran / 16 h / 20 °C

6.1: 1.28 g / TBAF / tetrahydrofuran / 3.5 h / 0 - 20 °C

7.1: Me₄NBH(OAc)3; AcOH / acetonitrile / cooling

8.1: 166.8 mg / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -20 °C

9.1: H₂ / Pd/C / methanol / 4 h / 20 °C

10.1: HOBt; EDC; N-methylmorpholine / CHCl₃ / 72 h / 20 °C

11.1: 137.0 mg / imidazole; DMAP / dimethylformamide / 40 h / 20 °C

12.1: aq. NaOH / methanol / 0 - 20 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; magnesium chloride; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile; 5.2: Claisen condensation;
DOI:10.1002/anie.200453909

Reference yield:

: 752251-09-5
(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester

: 752251-16-4
(3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: 78 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

2.1: 54 percent / aq. NaOH / tetrahydrofuran; methanol / 4 h / 0 - 20 °C

3.1: tetrahydrofuran / 1 h / 0 °C

4.1: MgCl₂ / tetrahydrofuran / 5 h / Heating

4.2: 3.38 g / tetrahydrofuran / 16 h / 20 °C

5.1: 1.28 g / TBAF / tetrahydrofuran / 3.5 h / 0 - 20 °C

6.1: Me₄NBH(OAc)3; AcOH / acetonitrile / cooling

7.1: 166.8 mg / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -20 °C

8.1: H₂ / Pd/C / methanol / 4 h / 20 °C

9.1: HOBt; EDC; N-methylmorpholine / CHCl₃ / 72 h / 20 °C

10.1: 137.0 mg / imidazole; DMAP / dimethylformamide / 40 h / 20 °C

11.1: aq. NaOH / methanol / 0 - 20 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; magnesium chloride; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile; 4.2: Claisen condensation;
DOI:10.1002/anie.200453909