(2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid ethyl ester

Base Information

Chemical Name:(2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid ethyl ester
CAS No.:477945-84-9
Molecular Formula:C₃₄H₅₂O₅Si
Molecular Weight:568.869
Hs Code.:

Synonyms:(2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid ethyl ester

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Chemical Property of (2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid ethyl ester

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Technology Process of (2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid ethyl ester

There total 10 articles about (2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid ethyl 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: 74.0%

: 477945-83-8
(S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-pentanoic acid ethyl ester

: 74-88-4
methyl iodide

: 477945-84-9
(2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid ethyl ester

Guidance literature:: (S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-pentanoic acid ethyl ester; With 2,2,6,6-tetramethylpiperidinyl-lithium; In tetrahydrofuran; at -78 ℃;

methyl iodide; In tetrahydrofuran; at -78 - 0 ℃;
DOI:10.1016/S0040-4039(02)01853-1

Reference yield:

: 196491-68-6
3-[dimethyl(phenyl)silyl]glutaric anhydride

: 477945-84-9
(2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: DMAP / CH₂Cl₂ / 20 °C

2.1: (COCl)2 / dimethylformamide; CH₂Cl₂ / 20 °C

3.1: diethyl ether / 0 °C

4.1: 78 percent / PhCO₂Ag; Et₃N / tetrahydrofuran / 20 °C

5.1: 98 percent / H₂ / Pd-C / ethyl acetate / 20 °C

6.1: Et₃N / tetrahydrofuran / 0 °C

7.1: tetrahydrofuran / -78 °C

8.1: TMSO-Tf / CH₂Cl₂ / -20 °C

9.1: Ti(OEt)4 / Heating

10.1: Li-TMP / tetrahydrofuran / -78 °C

10.2: 74 percent / tetrahydrofuran / -78 - 0 °C

With dmap; titanium(IV) tetraethanolate; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; silver benzoate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 4.1: Wolff rearrangement / 7.1: Grignard reaction;
DOI:10.1016/S0040-4039(02)01853-1

Reference yield:

: 5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid

: 477945-84-9
(2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: (COCl)2 / dimethylformamide; CH₂Cl₂ / 20 °C

2.1: diethyl ether / 0 °C

3.1: 78 percent / PhCO₂Ag; Et₃N / tetrahydrofuran / 20 °C

4.1: 98 percent / H₂ / Pd-C / ethyl acetate / 20 °C

5.1: Et₃N / tetrahydrofuran / 0 °C

6.1: tetrahydrofuran / -78 °C

7.1: TMSO-Tf / CH₂Cl₂ / -20 °C

8.1: Ti(OEt)4 / Heating

9.1: Li-TMP / tetrahydrofuran / -78 °C

9.2: 74 percent / tetrahydrofuran / -78 - 0 °C

With titanium(IV) tetraethanolate; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; silver benzoate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3.1: Wolff rearrangement / 6.1: Grignard reaction;
DOI:10.1016/S0040-4039(02)01853-1