(3S,5R)-3-[(t-butyldimethylsilyl)oxy]-5-[(t-butyldiphenylsilyl)oxy]-1-octen-7-yne

Base Information

Chemical Name:(3S,5R)-3-[(t-butyldimethylsilyl)oxy]-5-[(t-butyldiphenylsilyl)oxy]-1-octen-7-yne
CAS No.:152032-73-0
Molecular Formula:C₃₀H₄₄O₂Si₂
Molecular Weight:492.849
Hs Code.:

Synonyms:(3S,5R)-3-[(t-butyldimethylsilyl)oxy]-5-[(t-butyldiphenylsilyl)oxy]-1-octen-7-yne

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Chemical Property of (3S,5R)-3-[(t-butyldimethylsilyl)oxy]-5-[(t-butyldiphenylsilyl)oxy]-1-octen-7-yne

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Technology Process of (3S,5R)-3-[(t-butyldimethylsilyl)oxy]-5-[(t-butyldiphenylsilyl)oxy]-1-octen-7-yne

There total 6 articles about (3S,5R)-3-[(t-butyldimethylsilyl)oxy]-5-[(t-butyldiphenylsilyl)oxy]-1-octen-7-yne 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: 86.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 303015-30-7
(3S,5S)-5-[(t-butyldiphenylsilyl)oxy]-3-hydroxy-1-octen-7-yne

: 152032-73-0
(3S,5R)-3-[(t-butyldimethylsilyl)oxy]-5-[(t-butyldiphenylsilyl)oxy]-1-octen-7-yne

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 40 ℃; for 2h;
DOI:10.1016/S0968-0896(00)00142-5

Reference yield:

: 178751-54-7
(S)-2-hydroxy-5-trimethylsilyl-1-p-toluenesulfonyloxy-4-pentyne

: 152032-73-0
(3S,5R)-3-[(t-butyldimethylsilyl)oxy]-5-[(t-butyldiphenylsilyl)oxy]-1-octen-7-yne

Guidance literature:: Multi-step reaction with 6 steps

1: 72 percent / dimethylsulfoxide / 3 h / 40 °C

2: 90 percent / imidazole / dimethylformamide / 2 h / 40 °C

3: 412 g / DIBALH / CH₂Cl₂ / 0.5 h / -10 °C

4: 226 mg / tetrahydrofuran / 0.5 h / -70 - 20 °C

5: 55 percent / K₂CO₃ / methanol / 1 h / 20 °C

6: 86 percent / imidazole / dimethylformamide / 2 h / 40 °C

With 1H-imidazole; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Substitution / 2: silylation / 3: Reduction / 4: Grignard reaction / 5: desilylation / 6: silylation;
DOI:10.1016/S0968-0896(00)00142-5

Reference yield:

: 210906-84-6
(S)-1-cyano-2-hydroxy-5-trimethylsilyl-4-pentyne

: 152032-73-0
(3S,5R)-3-[(t-butyldimethylsilyl)oxy]-5-[(t-butyldiphenylsilyl)oxy]-1-octen-7-yne

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / imidazole / dimethylformamide / 2 h / 40 °C

2: 412 g / DIBALH / CH₂Cl₂ / 0.5 h / -10 °C

3: 226 mg / tetrahydrofuran / 0.5 h / -70 - 20 °C

4: 55 percent / K₂CO₃ / methanol / 1 h / 20 °C

5: 86 percent / imidazole / dimethylformamide / 2 h / 40 °C

With 1H-imidazole; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Reduction / 3: Grignard reaction / 4: desilylation / 5: silylation;
DOI:10.1016/S0968-0896(00)00142-5