(R)-1-tert-butyldimethylsilyloxy-3-(1-phenylsulfonylindol-2-yl)propan-2-ol

Base Information

Chemical Name:(R)-1-tert-butyldimethylsilyloxy-3-(1-phenylsulfonylindol-2-yl)propan-2-ol
CAS No.:252191-34-7
Molecular Formula:C₂₃H₃₁NO₄SSi
Molecular Weight:445.655
Hs Code.:

Synonyms:(R)-1-tert-butyldimethylsilyloxy-3-(1-phenylsulfonylindol-2-yl)propan-2-ol

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Chemical Property of (R)-1-tert-butyldimethylsilyloxy-3-(1-phenylsulfonylindol-2-yl)propan-2-ol

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Technology Process of (R)-1-tert-butyldimethylsilyloxy-3-(1-phenylsulfonylindol-2-yl)propan-2-ol

There total 2 articles about (R)-1-tert-butyldimethylsilyloxy-3-(1-phenylsulfonylindol-2-yl)propan-2-ol 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: 48.0%

: 40899-71-6
1-benzenesulfonylindole

: 124150-87-4
tert-butyldimethylsilyl (R)-glycidyl ether

: 252191-34-7
(R)-1-tert-butyldimethylsilyloxy-3-(1-phenylsulfonylindol-2-yl)propan-2-ol

Guidance literature:: 1-benzenesulfonylindole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 5 ℃; for 2.5h;

tert-butyldimethylsilyl (R)-glycidyl ether; In tetrahydrofuran; hexane; at -78 - 25 ℃;
DOI:10.1021/jo990242l

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 252191-34-7
(R)-1-tert-butyldimethylsilyloxy-3-(1-phenylsulfonylindol-2-yl)propan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 75 percent / triethylamine; DMAP / CH₂Cl₂ / 5 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - 5 °C

2.2: 48 percent / tetrahydrofuran; hexane / -78 - 25 °C

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: silylation / 2.1: Metallation / 2.2: Alkylation;
DOI:10.1021/jo990242l

Reference yield:

: 252191-34-7
(R)-1-tert-butyldimethylsilyloxy-3-(1-phenylsulfonylindol-2-yl)propan-2-ol

: 214150-14-8
C₅₄H₆₉N₆O₁₁PSi₂

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / KOH / methanol; H₂O / 5 h / Heating

2: 90 percent / pyridine / 5 h / 0 °C

3: LiCN / dimethylformamide / 1 h / 100 °C

4: PCl₃; triethylamine / tetrahydrofuran / 1.5 h / -78 - 0 °C

5: triethylamine / tetrahydrofuran / 0.5 h / -78 °C

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.17 h / 20 °C

With pyridine; potassium hydroxide; lithium cyanide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; phosphorus trichloride; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Tosylation / 3: Substitution / 4: Cyclization / 5: Substitution / 6: Esterification;
DOI:10.1021/jo990242l