(3aR,4S,6aR,10aS)-4-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-10-one

Base Information

Chemical Name:(3aR,4S,6aR,10aS)-4-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-10-one
CAS No.:78442-74-7
Molecular Formula:C₂₀H₂₆O₄S₂
Molecular Weight:394.556
Hs Code.:

Synonyms:(3aR,4S,6aR,10aS)-4-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-10-one

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Chemical Property of (3aR,4S,6aR,10aS)-4-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-10-one

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Technology Process of (3aR,4S,6aR,10aS)-4-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-10-one

There total 16 articles about (3aR,4S,6aR,10aS)-4-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-10-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:

: 31600-42-7
methyl 4-(benzyloxy)butanoate

: 78442-74-7
(3aR,4S,6aR,10aS)-4-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-10-one

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) i-PrNLi / 1.) THF, -78 deg C

2: conc. H₂SO₄ / methanol / 25 °C

3: LiAlH₄ / diethyl ether / -20 deg C -> 0 deg C

4: pyridine / 0 °C

5: NaH / tetrahydrofuran; dimethylsulfoxide / Ambient temperature

6: AcOH / H₂O / Ambient temperature

7: SiO₂

8: pyridine / Ambient temperature

9: alumina / ethyl acetate / Ambient temperature

10: NaBH₄ / methanol / 0 °C

11: KH / tetrahydrofuran / 0 °C

12: 1.) OsO₄, 2.) NaHSO₃ / 1.) Et₂O, room temperature, 2.) aq. pyridine, room temperature

13: TsOH / CH₂Cl₂ / 0 °C

14: CF₃COOH / CH₂Cl₂ / Ambient temperature

15: 1.) (CF₃CO)2O, Me₂SO, 2.) (i-Pr)2NEt / 1.) CH₂Cl₂, -60 deg C, 2.) -60 deg C -> 0 deg C

With pyridine; aluminum oxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; sulfuric acid; silica gel; potassium hydride; sodium hydride; toluene-4-sulfonic acid; sodium hydrogensulfite; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetic anhydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;
DOI:10.1021/ja00401a049

Reference yield:

: 10385-30-5
4-(benzyloxy)butanoic acid

: 78442-74-7
(3aR,4S,6aR,10aS)-4-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-10-one

Guidance literature:: Multi-step reaction with 16 steps

1: conc. H₂SO₄ / 25 °C

2: 1.) i-PrNLi / 1.) THF, -78 deg C

3: conc. H₂SO₄ / methanol / 25 °C

4: LiAlH₄ / diethyl ether / -20 deg C -> 0 deg C

5: pyridine / 0 °C

6: NaH / tetrahydrofuran; dimethylsulfoxide / Ambient temperature

7: AcOH / H₂O / Ambient temperature

8: SiO₂

9: pyridine / Ambient temperature

10: alumina / ethyl acetate / Ambient temperature

11: NaBH₄ / methanol / 0 °C

12: KH / tetrahydrofuran / 0 °C

13: 1.) OsO₄, 2.) NaHSO₃ / 1.) Et₂O, room temperature, 2.) aq. pyridine, room temperature

14: TsOH / CH₂Cl₂ / 0 °C

15: CF₃COOH / CH₂Cl₂ / Ambient temperature

16: 1.) (CF₃CO)2O, Me₂SO, 2.) (i-Pr)2NEt / 1.) CH₂Cl₂, -60 deg C, 2.) -60 deg C -> 0 deg C

With pyridine; aluminum oxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; sulfuric acid; silica gel; potassium hydride; sodium hydride; toluene-4-sulfonic acid; sodium hydrogensulfite; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetic anhydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;
DOI:10.1021/ja00401a049

Reference yield:

: 4-Benzyloxy-2-dimethoxymethyl-butan-1-ol

: 78442-74-7
(3aR,4S,6aR,10aS)-4-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-10-one

Guidance literature:: Multi-step reaction with 12 steps

1: pyridine / 0 °C

2: NaH / tetrahydrofuran; dimethylsulfoxide / Ambient temperature

3: AcOH / H₂O / Ambient temperature

4: SiO₂

5: pyridine / Ambient temperature

6: alumina / ethyl acetate / Ambient temperature

7: NaBH₄ / methanol / 0 °C

8: KH / tetrahydrofuran / 0 °C

9: 1.) OsO₄, 2.) NaHSO₃ / 1.) Et₂O, room temperature, 2.) aq. pyridine, room temperature

10: TsOH / CH₂Cl₂ / 0 °C

11: CF₃COOH / CH₂Cl₂ / Ambient temperature

12: 1.) (CF₃CO)2O, Me₂SO, 2.) (i-Pr)2NEt / 1.) CH₂Cl₂, -60 deg C, 2.) -60 deg C -> 0 deg C

With pyridine; aluminum oxide; sodium tetrahydroborate; osmium(VIII) oxide; silica gel; potassium hydride; sodium hydride; toluene-4-sulfonic acid; sodium hydrogensulfite; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;
DOI:10.1021/ja00401a049