tert-butyl (3S,4R)-5-(tert-butyldiphenylsilyl)oxy-4-hydroxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxypentanoate

Base Information

• Chemical Name: tert-butyl (3S,4R)-5-(tert-butyldiphenylsilyl)oxy-4-hydroxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxypentanoate
• CAS No.: 1402749-91-0
• Molecular Formula: C₃₁H₄₄O₇Si
• Molecular Weight: 556.772

Synonyms:tert-butyl (3S,4R)-5-(tert-butyldiphenylsilyl)oxy-4-hydroxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxypentanoate

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about tert-butyl (3S,4R)-5-(tert-butyldiphenylsilyl)oxy-4-hydroxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxypentanoate 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: 96.0%

tert-butyl (3S,4R)-4,5-dihydroxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxypentanoate (1402749-90-9) + tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyl (3S,4R)-5-(tert-butyldiphenylsilyl)oxy-4-hydroxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxypentanoate (1402749-91-0)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1002/chem.201200542

Reference yield:

(3S,4R)-3-[(Z)-4-(tert-butyldiphenylsilyl)oxy-2-buten-1-yl]oxy-4,5-(dimethylmethylenedioxy)pentanal (914093-22-4) → tert-butyl (3S,4R)-5-(tert-butyldiphenylsilyl)oxy-4-hydroxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxypentanoate (1402749-91-0)

Guidance literature:

Multi-step reaction with 9 steps

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

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

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

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

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

5.2: 20 h / 20 °C / Inert atmosphere

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

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

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

9.1: 1H-imidazole / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; hydrogen; potassium carbonate; acetic acid; In tetrahydrofuran; 2-methyl-but-2-ene; dichloromethane; water; acetic acid; ethyl acetate; acetone; tert-butyl alcohol; 4.1: Swern oxidation;

DOI:10.1002/chem.201200542

Reference yield:

tert-butyl (3S,4R)-3-[4-(tert-butyldiphenylsilyl)oxybutyl]oxy-4,5-(dimethylmethylenedioxy)pentanoate (914093-09-7) → tert-butyl (3S,4R)-5-(tert-butyldiphenylsilyl)oxy-4-hydroxy-3-[3-(methoxycarbonyl)-3-buten-1-yl]oxypentanoate (1402749-91-0)

Guidance literature:

Multi-step reaction with 6 steps

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

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

2.2: 20 h / 20 °C / Inert atmosphere

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

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

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

6.1: 1H-imidazole / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; tetrabutyl ammonium fluoride; water; potassium carbonate; acetic acid; In tetrahydrofuran; 2-methyl-but-2-ene; dichloromethane; water; acetic acid; acetone; tert-butyl alcohol; 1.1: Swern oxidation;

DOI:10.1002/chem.201200542

upstream raw materials:

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

tert-butyl (3S,4R)-3-[4-(tert-butyldiphenylsilyl)oxybutyl]oxy-4,5-(dimethylmethylenedioxy)pentanoate

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

Downstream raw materials:

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

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