(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one

Base Information

Chemical Name:(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one
CAS No.:891491-89-7
Molecular Formula:C₂₂H₂₄O₄Se
Molecular Weight:431.39
Hs Code.:

Synonyms:(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one

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Chemical Property of (6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one

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Technology Process of (6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one

There total 14 articles about (6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one 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:

: 5707-04-0
Phenylselenyl chloride

: 216769-26-5
(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-pyran-2-one

: 891491-89-7
(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1039/a806584e

Reference yield:

: 216769-01-6
(R)-6-(tert-butyldiphenylsilanyloxymethyl)-tetrahydropyran-2-ol

: 891491-89-7
(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: 81 percent / KHMDS / toluene; tetrahydrofuran / 2 h / -78 - 0 °C

2.1: 97 percent / tetrahydrofuran; diethyl ether / 0.5 h / -30 °C

3.1: Et₃N / CH₂Cl₂ / -78 - -30 °C

4.1: 1.13 g / TMSOTf / CH₂Cl₂ / 0.17 h / -30 °C

5.1: 100 percent / NaBH₄ / methanol / 0.02 h / 0 °C

6.1: 99 percent / (+/-)-camphorsulfonic acid / acetone / 0.5 h

7.1: 99 percent / TBAF / tetrahydrofuran / 2 h

8.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

9.1: 1,2-dimethoxyprop-1-ene; sodium perchlorite; aq. KH₂PO₄ / 2-methyl-propan-2-ol / 0.17 h

10.1: 0.061 g / pyridine / tetrahydrofuran / 0.5 h / 20 °C

11.1: NaOMe / methanol / 0.17 h

12.1: 0.084 g / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h

13.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

13.2: tetrahydrofuran; hexane / 1 h / -78 °C

With pyridine; sodium tetrahydroborate; potassium dihydrogenphosphate; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; potassium hexamethylsilazane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; tert-butyl alcohol;
DOI:10.1039/b602805e

Reference yield:

: 216769-05-0
(R,R)-2-(6'-tert-butyldiphenylsilanyloxymethylpyranyloxy)-1-phenylethanone

: 891491-89-7
(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: Et₃N / CH₂Cl₂ / -78 - -30 °C

2.1: 1.13 g / TMSOTf / CH₂Cl₂ / 0.17 h / -30 °C

3.1: 100 percent / NaBH₄ / methanol / 0.02 h / 0 °C

4.1: 99 percent / (+/-)-camphorsulfonic acid / acetone / 0.5 h

5.1: 99 percent / TBAF / tetrahydrofuran / 2 h

6.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: 1,2-dimethoxyprop-1-ene; sodium perchlorite; aq. KH₂PO₄ / 2-methyl-propan-2-ol / 0.17 h

8.1: 0.061 g / pyridine / tetrahydrofuran / 0.5 h / 20 °C

9.1: NaOMe / methanol / 0.17 h

10.1: 0.084 g / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h

11.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

11.2: tetrahydrofuran; hexane / 1 h / -78 °C

With pyridine; sodium tetrahydroborate; potassium dihydrogenphosphate; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; tert-butyl alcohol;
DOI:10.1039/b602805e