(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl ester

Base Information

Chemical Name:(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl ester
CAS No.:503446-41-1
Molecular Formula:C₃₅H₅₁BrO₅
Molecular Weight:631.691
Hs Code.:

Synonyms:(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl ester

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Chemical Property of (4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl ester

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Technology Process of (4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl ester

There total 2 articles about (4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl 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: 90.0%

: 503446-40-0
(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester

: 503446-41-1
(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl ester

Guidance literature:: With Amberlyst 15; In water; acetone;
DOI:10.1016/S0040-4039(02)02603-5

Reference yield:

: (4R,5R,8S,12R)-4,7-Bis-benzyloxy-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester

: 503446-41-1
(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: LDA; TMSCl; Et₃N / tetrahydrofuran / -78 °C

1.2: 90 percent / NBS / 20 °C

2.1: 90 percent / Amberlyst 15 / acetone; H₂O

With chloro-trimethyl-silane; Amberlyst 15; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; water; acetone;
DOI:10.1016/S0040-4039(02)02603-5

Reference yield:

: 503446-41-1
(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl ester

: 503546-23-4
(4R,5R,7S,8S,12R)-4,7-Bis-benzyloxy-5-isopropyl-8,12-dimethyl-15-oxa-bicyclo[12.1.0]pentadecane-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: SmI₂ / tetrahydrofuran / 0 °C

2: Et₃N / CH₂Cl₂ / 20 °C

3: DBU / toluene / 10 h / Heating

4: 70 percent / mCPBA / CH₂Cl₂ / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; samarium diiodide; In tetrahydrofuran; dichloromethane; toluene; 1: intramolecular Reformatsky reaction;
DOI:10.1016/S0040-4039(02)02603-5