(2S)-4-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane

Base Information

• Chemical Name: (2S)-4-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane
• CAS No.: 618388-44-6
• Molecular Formula: C₃₄H₄₇NO₄Si₂
• Molecular Weight: 589.922
• Mol file: 618388-44-6.mol

Synonyms:(2S)-4-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane

Chemical Property of (2S)-4-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-4-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane

There total 6 articles about (2S)-4-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane 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: 94.0%

(S)-4-phthalimido-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane (287728-23-8) → (2S)-4-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane (618388-44-6)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -40 - -20 ℃;

DOI:10.1039/b303031h

Reference yield:

phthalimide (136918-14-4,85-41-6) → (2S)-4-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane (618388-44-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

2: 85 percent / aq. HCl / tetrahydrofuran / 0.5 h / 60 °C

3: 97 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

4: imidazole / CH₂Cl₂; dimethylformamide / 20 °C

5: 94 percent / NaBH₄ / methanol; tetrahydrofuran / -40 - -20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Mitsunobu reaction;

DOI:10.1039/b303031h

Reference yield:

(S)-4-phthalimido-1-(tert-butyldimethylsilyloxy)butan-2-ol (287728-32-9) → (2S)-4-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane (618388-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / CH₂Cl₂; dimethylformamide / 20 °C

2: 94 percent / NaBH₄ / methanol; tetrahydrofuran / -40 - -20 °C

With 1H-imidazole; sodium tetrahydroborate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b303031h

upstream raw materials:

(S)-4-phthalimido-2-(tert-butyldiphenylsilyl)oxy-1-(tert-butyldimethylsilyl)oxybutane

phthalimide

(S)-4-phthalimido-1,2-butanediol

(S)-2,2-dimethyl-4-(2-phthalimidoethyl)-1,3-dioxolane

Downstream raw materials:

4-(1-allyl-3-oxo-1-phenylsulfanyl-1,3-dihydro-isoindol-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde

2-[4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-3-phenylsulfanyl-2,3-dihydro-isoindol-1-one