(S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-yl (S)-2-methoxy-2-phenylacetate

Base Information

Chemical Name:(S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-yl (S)-2-methoxy-2-phenylacetate
CAS No.:1477482-31-7
Molecular Formula:C₃₃H₄₂O₄Si₂
Molecular Weight:558.865
Hs Code.:

Synonyms:(S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-yl (S)-2-methoxy-2-phenylacetate

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Chemical Property of (S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-yl (S)-2-methoxy-2-phenylacetate

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Technology Process of (S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-yl (S)-2-methoxy-2-phenylacetate

There total 4 articles about (S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-yl (S)-2-methoxy-2-phenylacetate 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: 95.0%

: 26164-26-1
(S)-2-methoxy-2-phenylacetic acid

: 225114-87-4
(S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-ol

: 1477482-31-7
(S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-yl (S)-2-methoxy-2-phenylacetate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/acs.joc.8b03249

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1477482-31-7
(S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-yl (S)-2-methoxy-2-phenylacetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / nujol; tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere

1.2: 1 h / 0 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

3.1: (R)-1,1'-Bi-2-naphthol; diethylzinc; titanium(IV) isopropylate / dichloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane / 2 h / 20 °C

3.2: 12 h / 20 °C

4.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.75 h

With titanium(IV) isopropylate; dmap; oxalyl dichloride; diethylzinc; (R)-1,1'-Bi-2-naphthol; sodium hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; nujol; hexane; dichloromethane; 2.2: |Swern Oxidation;
DOI:10.1055/s-0033-1339493

Reference yield:

: 127047-71-6
3-(tert-butyldiphenylsilyloxy)propan-1-ol

: 1477482-31-7
(S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-yl (S)-2-methoxy-2-phenylacetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

1.2: -78 °C / Inert atmosphere

2.1: (R)-1,1'-Bi-2-naphthol; diethylzinc; titanium(IV) isopropylate / dichloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane / 2 h / 20 °C

2.2: 12 h / 20 °C

3.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.75 h

With titanium(IV) isopropylate; dmap; oxalyl dichloride; diethylzinc; (R)-1,1'-Bi-2-naphthol; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; 1.2: |Swern Oxidation;
DOI:10.1055/s-0033-1339493