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

Base Information

• Chemical Name: (2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid amide
• CAS No.: 477945-85-0
• Molecular Formula: C₃₂H₄₉NO₄Si
• Molecular Weight: 539.831

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 12 articles about (2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid amide 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:

(2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid → (2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid amide (477945-85-0)

Guidance literature:

(2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃;

With ammonia;

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 → (2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid amide (477945-85-0)

Guidance literature:

Multi-step reaction with 11 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

10.1: KOH / methanol; H₂O / Heating

11.1: (Im)2CO / CH₂Cl₂ / 20 °C

11.2: NH₃

With titanium(IV) tetraethanolate; potassium hydroxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; silver benzoate; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 3.1: Wolff rearrangement / 6.1: Grignard reaction;

DOI:10.1016/S0040-4039(02)01853-1

Reference yield:

3-[dimethyl(phenyl)silyl]glutaric anhydride (196491-68-6) → (2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid amide (477945-85-0)

Guidance literature:

Multi-step reaction with 12 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

11.1: KOH / methanol; H₂O / Heating

12.1: (Im)2CO / CH₂Cl₂ / 20 °C

12.2: NH₃

With dmap; titanium(IV) tetraethanolate; potassium hydroxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; silver benzoate; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 4.1: Wolff rearrangement / 7.1: Grignard reaction;

DOI:10.1016/S0040-4039(02)01853-1

upstream raw materials:

3-[dimethyl(phenyl)silyl]glutaric anhydride

(S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-6-diazo-3-(dimethyl-phenyl-silanyl)-hexane-1,5-dione

(S)-6-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-4-(dimethyl-phenyl-silanyl)-6-oxo-hexanoic acid

(S)-6-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-4-(dimethyl-phenyl-silanyl)-6-oxo-hexanoic acid benzyl ester

Downstream raw materials:

[(1S,2S)-4-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-2-(dimethyl-phenyl-silanyl)-1-methyl-butyl]-carbamic acid benzyl ester

8-{(2S,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidinyl}octanoic acid

8-[(2R,5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-methyl-piperidin-2-yl]-octan-1-ol

(2S,3S,6R)-3-(Dimethyl-phenyl-silanyl)-6-(8-hydroxy-octyl)-2-methyl-piperidine-1-carboxylic acid benzyl ester

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