(E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:(E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester
CAS No.:503446-45-5
Molecular Formula:C₃₅H₅₀O₅
Molecular Weight:550.779
Hs Code.:

Synonyms:(E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester

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Chemical Property of (E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester

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Technology Process of (E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester

There total 8 articles about (E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic 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: 70.0%

: 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

: 503446-45-5
(E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester

Guidance literature:: With sodium methylate; In methanol;
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

: 503446-45-5
(E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: SmI₂ / tetrahydrofuran / 0 °C

2: Et₃N / CH₂Cl₂ / 20 °C

3: DBU / toluene / 10 h / Heating

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

5: 70 percent / CH₃ONa / methanol

With sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; samarium diiodide; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: intramolecular Reformatsky reaction;
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

: 503446-45-5
(E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

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

1.2: 90 percent / NBS / 20 °C

2.1: 90 percent / Amberlyst 15 / acetone; H₂O

3.1: SmI₂ / tetrahydrofuran / 0 °C

4.1: Et₃N / CH₂Cl₂ / 20 °C

5.1: DBU / toluene / 10 h / Heating

6.1: 70 percent / mCPBA / CH₂Cl₂ / 20 °C

7.1: 70 percent / CH₃ONa / methanol

With chloro-trimethyl-silane; Amberlyst 15; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; samarium diiodide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 3.1: intramolecular Reformatsky reaction;
DOI:10.1016/S0040-4039(02)02603-5