(3aS,8R,8aS,9aR)-8-Benzyloxymethyl-2,2-dimethyl-3a,4,8,8a,9,9a-hexahydro-1,3-dioxa-4a-aza-cyclopenta[b]naphthalen-5-one

Base Information

Chemical Name:(3aS,8R,8aS,9aR)-8-Benzyloxymethyl-2,2-dimethyl-3a,4,8,8a,9,9a-hexahydro-1,3-dioxa-4a-aza-cyclopenta[b]naphthalen-5-one
CAS No.:753452-04-9
Molecular Formula:C₂₀H₂₅NO₄
Molecular Weight:343.423
Hs Code.:

Synonyms:(3aS,8R,8aS,9aR)-8-Benzyloxymethyl-2,2-dimethyl-3a,4,8,8a,9,9a-hexahydro-1,3-dioxa-4a-aza-cyclopenta[b]naphthalen-5-one

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Chemical Property of (3aS,8R,8aS,9aR)-8-Benzyloxymethyl-2,2-dimethyl-3a,4,8,8a,9,9a-hexahydro-1,3-dioxa-4a-aza-cyclopenta[b]naphthalen-5-one

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Technology Process of (3aS,8R,8aS,9aR)-8-Benzyloxymethyl-2,2-dimethyl-3a,4,8,8a,9,9a-hexahydro-1,3-dioxa-4a-aza-cyclopenta[b]naphthalen-5-one

There total 10 articles about (3aS,8R,8aS,9aR)-8-Benzyloxymethyl-2,2-dimethyl-3a,4,8,8a,9,9a-hexahydro-1,3-dioxa-4a-aza-cyclopenta[b]naphthalen-5-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: 92.0%

: 77-76-9
2,2-dimethoxy-propane

: 753452-02-7
(1R,7S,8R,9aS)-1-Benzyloxymethyl-7,8-dihydroxy-1,6,7,8,9,9a-hexahydro-quinolizin-4-one

: 753452-04-9
(3aS,8R,8aS,9aR)-8-Benzyloxymethyl-2,2-dimethyl-3a,4,8,8a,9,9a-hexahydro-1,3-dioxa-4a-aza-cyclopenta[b]naphthalen-5-one

Guidance literature:: With toluene-4-sulfonic acid; at 0 ℃; for 2h;
DOI:10.1002/chem.200305581

Reference yield:

: (2S,3R)-2-Vinyl-hex-5-ene-1,3-diol

: 753452-04-9
(3aS,8R,8aS,9aR)-8-Benzyloxymethyl-2,2-dimethyl-3a,4,8,8a,9,9a-hexahydro-1,3-dioxa-4a-aza-cyclopenta[b]naphthalen-5-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / -78 - 20 °C

2.1: 97 percent / Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

3.1: NaN₃ / hexamethylphosphoric acid triamide / 2 h / 40 °C

3.2: 93 percent / TBAF / tetrahydrofuran

4.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

4.2: 97 percent / tetrahydrofuran / 3.5 h / 20 °C

5.1: LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

6.1: 1.48 g / K₂CO₃ / dimethylformamide / 1.5 h / 0 - 20 °C

7.1: 91 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: 60 percent / PhCH=RuCH[(Mes)NCH₂CH₂N(Mes)](PCy₃)Cl₂ / CH₂Cl₂ / 6 h / Heating

9.1: 82 percent / [K₃Fe(CN)6]; aq. K₂CO₃; CH₃SO₃NH₂ / DHQ-PHAL; K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 4 h / 0 °C

10.1: 92 percent / TsOH*H₂O / 2 h / 0 °C

With dmap; potassium hexacyanoferrate (III); lithium aluminium tetrahydride; sodium azide; sulfamic acid methyl ester; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium dioxotetrahydroxoosmate(VI); DHQ-PHAL; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/chem.200305581

Reference yield:

: ((2R,3S)-3-Azido-2-vinyl-hex-5-enyloxymethyl)-benzene

: 753452-04-9
(3aS,8R,8aS,9aR)-8-Benzyloxymethyl-2,2-dimethyl-3a,4,8,8a,9,9a-hexahydro-1,3-dioxa-4a-aza-cyclopenta[b]naphthalen-5-one

Guidance literature:: Multi-step reaction with 6 steps

1: LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

2: 1.48 g / K₂CO₃ / dimethylformamide / 1.5 h / 0 - 20 °C

3: 91 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

4: 60 percent / PhCH=RuCH[(Mes)NCH₂CH₂N(Mes)](PCy₃)Cl₂ / CH₂Cl₂ / 6 h / Heating

5: 82 percent / [K₃Fe(CN)6]; aq. K₂CO₃; CH₃SO₃NH₂ / DHQ-PHAL; K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 4 h / 0 °C

6: 92 percent / TsOH*H₂O / 2 h / 0 °C

With potassium hexacyanoferrate (III); lithium aluminium tetrahydride; sulfamic acid methyl ester; potassium carbonate; toluene-4-sulfonic acid; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium dioxotetrahydroxoosmate(VI); DHQ-PHAL; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/chem.200305581