tert-butyl (S)-5-(tert-butyldiphenylsilyl)oxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxy-4-oxopentanoate

Base Information

• Chemical Name: tert-butyl (S)-5-(tert-butyldiphenylsilyl)oxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxy-4-oxopentanoate
• CAS No.: 1402749-88-5
• Molecular Formula: C₃₁H₄₂O₇Si
• Molecular Weight: 554.756

Synonyms:tert-butyl (S)-5-(tert-butyldiphenylsilyl)oxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxy-4-oxopentanoate

Chemical Property of tert-butyl (S)-5-(tert-butyldiphenylsilyl)oxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxy-4-oxopentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S)-5-(tert-butyldiphenylsilyl)oxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxy-4-oxopentanoate

There total 10 articles about tert-butyl (S)-5-(tert-butyldiphenylsilyl)oxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxy-4-oxopentanoate 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: 92.0%

tert-butyl (3S,4R)-5-(tert-butyldiphenylsilyl)oxy-4-hydroxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxypentanoate (1402749-91-0) → tert-butyl (S)-5-(tert-butyldiphenylsilyl)oxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxy-4-oxopentanoate (1402749-88-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 1h; Inert atmosphere;

DOI:10.1002/chem.201200542

Reference yield:

tert-butyl (3S,4R)-3-[(Z)-4-(tert-butyldiphenylsilyl)oxy-2-buten-1-yl]oxy-4,5-(dimethylmethylenedioxy)pentanoate (914093-08-6) → tert-butyl (S)-5-(tert-butyldiphenylsilyl)oxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxy-4-oxopentanoate (1402749-88-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 13 h / 760.05 Torr / Inert atmosphere

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

3.1: oxalyl dichloride / dichloromethane / -78 - 0 °C / Inert atmosphere

3.2: 20 h / 20 °C / Inert atmosphere

4.1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 7 h / Inert atmosphere

5.1: potassium carbonate / acetone / 14 h / Inert atmosphere

6.1: water / tetrahydrofuran; acetic acid / 6 h / 40 °C / Inert atmosphere

7.1: 1H-imidazole / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere

8.1: Dess-Martin periodane / dichloromethane / 1 h / Inert atmosphere

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; hydrogen; potassium carbonate; Dess-Martin periodane; acetic acid; In tetrahydrofuran; 2-methyl-but-2-ene; dichloromethane; water; acetic acid; ethyl acetate; acetone; tert-butyl alcohol; 2.1: Swern oxidation / 8.1: Dess-Martin oxidation;

DOI:10.1002/chem.201200542

Reference yield:

(3S,4R)-3-[(Z)-4-(tert-butyldiphenylsilyl)oxy-2-buten-1-yl]oxy-4,5-(dimethylmethylenedioxy)-1,1-bis(ethylthio)pentane (914093-07-5) → tert-butyl (S)-5-(tert-butyldiphenylsilyl)oxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxy-4-oxopentanoate (1402749-88-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: iodine; sodium hydrogencarbonate / water; acetone / 0.08 h / -25 °C / Inert atmosphere

2.1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 6 h / Inert atmosphere

3.1: dmap / tert-butyl alcohol / 1 h / 20 °C

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 13 h / 760.05 Torr / Inert atmosphere

5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

6.1: oxalyl dichloride / dichloromethane / -78 - 0 °C / Inert atmosphere

6.2: 20 h / 20 °C / Inert atmosphere

7.1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 7 h / Inert atmosphere

8.1: potassium carbonate / acetone / 14 h / Inert atmosphere

9.1: water / tetrahydrofuran; acetic acid / 6 h / 40 °C / Inert atmosphere

10.1: 1H-imidazole / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere

11.1: Dess-Martin periodane / dichloromethane / 1 h / Inert atmosphere

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; hydrogen; iodine; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; In tetrahydrofuran; 2-methyl-but-2-ene; dichloromethane; water; acetic acid; ethyl acetate; acetone; tert-butyl alcohol; 5.1: Swern oxidation / 11.1: Dess-Martin oxidation;

DOI:10.1002/chem.201200542

upstream raw materials:

tert-butyl (3S,4R)-4,5-(dimethylmethylenedioxy)-3-(3-formyl-3-buten-1-yl)oxypentanoate

(3S,4R)-3-[(Z)-4-(tert-butyldiphenylsilyl)oxy-2-buten-1-yl]oxy-4,5-(dimethylmethylenedioxy)pentanal

tert-butyl (3S,4R)-3-[(Z)-4-(tert-butyldiphenylsilyl)oxy-2-buten-1-yl]oxy-4,5-(dimethylmethylenedioxy)pentanoate

(3S,4R)-3-[(Z)-4-(tert-butyldiphenylsilyl)oxy-2-buten-1-yl]oxy-4,5-(dimethylmethylenedioxy)-1,1-bis(ethylthio)pentane

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