(3aR,4aS,7aS,8S,9aR)-4a-Benzyloxymethyl-8-methyl-decahydro-azuleno[6,5-b]furan-2,5-dione

Base Information

Chemical Name:(3aR,4aS,7aS,8S,9aR)-4a-Benzyloxymethyl-8-methyl-decahydro-azuleno[6,5-b]furan-2,5-dione
CAS No.:107163-96-2
Molecular Formula:C₂₁H₂₆O₄
Molecular Weight:342.435
Hs Code.:

Synonyms:(3aR,4aS,7aS,8S,9aR)-4a-Benzyloxymethyl-8-methyl-decahydro-azuleno[6,5-b]furan-2,5-dione

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Chemical Property of (3aR,4aS,7aS,8S,9aR)-4a-Benzyloxymethyl-8-methyl-decahydro-azuleno[6,5-b]furan-2,5-dione

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Technology Process of (3aR,4aS,7aS,8S,9aR)-4a-Benzyloxymethyl-8-methyl-decahydro-azuleno[6,5-b]furan-2,5-dione

There total 17 articles about (3aR,4aS,7aS,8S,9aR)-4a-Benzyloxymethyl-8-methyl-decahydro-azuleno[6,5-b]furan-2,5-dione 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:

4-hexyn-1-ol: 928-93-8
4-hexyn-1-ol

: 107163-96-2
(3aR,4aS,7aS,8S,9aR)-4a-Benzyloxymethyl-8-methyl-decahydro-azuleno[6,5-b]furan-2,5-dione

Guidance literature:: Multi-step reaction with 18 steps

1: H₂ / Pd/CaCO₃, (Lindlar),quinoline / pentane / 25 °C / 517.1 - 2068.6 Torr

2: 54 percent / PCC / CH₂Cl₂ / 2 h / 0 - 25 °C

3: 1.) Mg / 2.) THF, 0deg C, 1.5 h

4: 97 percent / DMAP, Et₃N / dimethylformamide / 10 h / 25 °C

5: pentane / 25 °C / Irradiation

6: 71 percent / Hg(OAc)2 / tetrahydrofuran; H₂O / 0.25 h / 25 °C

7: 94 percent / NaBH₄ / methanol / 0.25 h / 25 °C

8: 93 percent / MnO₂ / CH₂Cl₂ / 24 h / 25 °C

9: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 °C / 760 Torr

10: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 °C

12: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 °C

13: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC

14: 97 percent / imidazole / dimethylformamide / 5 h / 25 °C

15: 1.) MsCl, pyridine, 2.) LAH / 1. 25 gradC, 17 h.; 2. DME, 0 gradC to 25 gradC, 17 h.

16: 96 percent / KH / tetrahydrofuran / 1.5 h / 25 °C

17: 1.) HF/H₂O, 2.) Jones reagent / 1. CH₃CN, THF, 25 gradC, 3 h; 2. CH₃COCH₃, 0 gradC to 25 gradC, 15 min.

18: 1. I₂, 2,4,6-collidine, CH₃CN, 25 gradC, 35 min; 2. Bu₃SnH, AIBN, PhH, 80 gradC, 6 h.

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; cerium(III) chloride; hydrogen fluoride; mercury(II) diacetate; water; hydrogen; potassium hydride; ozone; magnesium; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; quinoline; palladium on activated charcoal; Lindlar's catalyst; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1016/S0040-4039(00)84394-4

Reference yield:

: 4634-89-3
cis-hex-4-enal

: 107163-96-2
(3aR,4aS,7aS,8S,9aR)-4a-Benzyloxymethyl-8-methyl-decahydro-azuleno[6,5-b]furan-2,5-dione

Guidance literature:: Multi-step reaction with 16 steps

1: 1.) Mg / 2.) THF, 0deg C, 1.5 h

2: 97 percent / DMAP, Et₃N / dimethylformamide / 10 h / 25 °C

3: pentane / 25 °C / Irradiation

4: 71 percent / Hg(OAc)2 / tetrahydrofuran; H₂O / 0.25 h / 25 °C

5: 94 percent / NaBH₄ / methanol / 0.25 h / 25 °C

6: 93 percent / MnO₂ / CH₂Cl₂ / 24 h / 25 °C

7: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 °C / 760 Torr

8: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 °C

10: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 °C

11: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC

12: 97 percent / imidazole / dimethylformamide / 5 h / 25 °C

13: 1.) MsCl, pyridine, 2.) LAH / 1. 25 gradC, 17 h.; 2. DME, 0 gradC to 25 gradC, 17 h.

14: 96 percent / KH / tetrahydrofuran / 1.5 h / 25 °C

15: 1.) HF/H₂O, 2.) Jones reagent / 1. CH₃CN, THF, 25 gradC, 3 h; 2. CH₃COCH₃, 0 gradC to 25 gradC, 15 min.

16: 1. I₂, 2,4,6-collidine, CH₃CN, 25 gradC, 35 min; 2. Bu₃SnH, AIBN, PhH, 80 gradC, 6 h.

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; cerium(III) chloride; hydrogen fluoride; mercury(II) diacetate; water; hydrogen; potassium hydride; ozone; magnesium; methanesulfonyl chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1016/S0040-4039(00)84394-4

Reference yield:

: 107163-88-2
(Z)-1-(2-Methoxy-phenyl)-hex-4-en-1-ol

: 107163-96-2
(3aR,4aS,7aS,8S,9aR)-4a-Benzyloxymethyl-8-methyl-decahydro-azuleno[6,5-b]furan-2,5-dione

Guidance literature:: Multi-step reaction with 15 steps

1: 97 percent / DMAP, Et₃N / dimethylformamide / 10 h / 25 °C

2: pentane / 25 °C / Irradiation

3: 71 percent / Hg(OAc)2 / tetrahydrofuran; H₂O / 0.25 h / 25 °C

4: 94 percent / NaBH₄ / methanol / 0.25 h / 25 °C

5: 93 percent / MnO₂ / CH₂Cl₂ / 24 h / 25 °C

6: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 °C / 760 Torr

7: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 °C

9: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 °C

10: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC

11: 97 percent / imidazole / dimethylformamide / 5 h / 25 °C

12: 1.) MsCl, pyridine, 2.) LAH / 1. 25 gradC, 17 h.; 2. DME, 0 gradC to 25 gradC, 17 h.

13: 96 percent / KH / tetrahydrofuran / 1.5 h / 25 °C

14: 1.) HF/H₂O, 2.) Jones reagent / 1. CH₃CN, THF, 25 gradC, 3 h; 2. CH₃COCH₃, 0 gradC to 25 gradC, 15 min.

15: 1. I₂, 2,4,6-collidine, CH₃CN, 25 gradC, 35 min; 2. Bu₃SnH, AIBN, PhH, 80 gradC, 6 h.

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; cerium(III) chloride; hydrogen fluoride; mercury(II) diacetate; water; hydrogen; potassium hydride; ozone; methanesulfonyl chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1016/S0040-4039(00)84394-4