(3aR,4S,8R,8aR)-8a-Hydroxy-3a-methyl-7-methylene-3-oxo-9-trimethylsilanyloxy-octahydro-4,8-methano-azulene-4-carboxylic acid methyl ester

Base Information

Chemical Name:(3aR,4S,8R,8aR)-8a-Hydroxy-3a-methyl-7-methylene-3-oxo-9-trimethylsilanyloxy-octahydro-4,8-methano-azulene-4-carboxylic acid methyl ester
CAS No.:82891-03-0
Molecular Formula:C₁₈H₂₈O₅Si
Molecular Weight:352.503
Hs Code.:

Synonyms:(3aR,4S,8R,8aR)-8a-Hydroxy-3a-methyl-7-methylene-3-oxo-9-trimethylsilanyloxy-octahydro-4,8-methano-azulene-4-carboxylic acid methyl ester

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Chemical Property of (3aR,4S,8R,8aR)-8a-Hydroxy-3a-methyl-7-methylene-3-oxo-9-trimethylsilanyloxy-octahydro-4,8-methano-azulene-4-carboxylic acid methyl ester

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Technology Process of (3aR,4S,8R,8aR)-8a-Hydroxy-3a-methyl-7-methylene-3-oxo-9-trimethylsilanyloxy-octahydro-4,8-methano-azulene-4-carboxylic acid methyl ester

There total 1 articles about (3aR,4S,8R,8aR)-8a-Hydroxy-3a-methyl-7-methylene-3-oxo-9-trimethylsilanyloxy-octahydro-4,8-methano-azulene-4-carboxylic acid methyl ester 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: 42.9%

: 58274-64-9,82223-93-6,73912-36-4
(E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane

: 82891-01-8
2-methyl-2-<1-(methoxycarbonyl)ethen-1-yl>-1,3-cyclopentanedione

: 82891-03-0
(1S^*,2R^*,6R^*,7R^*,11S^*)-6-hydroxy-2-methyl-1-(methoxycarbonyl)-8-methylene-3-oxo-11-(trimethylsiloxy)tricyclo<5.3.1.0^2,6>undecane

: 82902-13-4
(3R^*,4R^*)-1-methyl-4-(2-methyl-1,3-dioxocyclopentan-2-yl)-4-(methoxycarbonyl)-3-(trimethylsiloxy)-1-cyclohexene

: 87902-39-4
(3aR,4aR,8aS,8bR)-6,8b-Dimethyl-1-oxo-3a-trimethylsilanyloxy-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester

: 87936-46-7
(3aR,4aS,8aR,8bR)-6,8b-Dimethyl-1-oxo-3a-trimethylsilanyloxy-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester

Guidance literature:: With benzenesulfonamide; In 1,3,5-trimethyl-benzene; 155 deg C, 5 h, reflux, 7 h;
DOI:10.1021/ja00314a023

Reference yield:

: 82891-03-0
(1S^*,2R^*,6R^*,7R^*,11S^*)-6-hydroxy-2-methyl-1-(methoxycarbonyl)-8-methylene-3-oxo-11-(trimethylsiloxy)tricyclo<5.3.1.0^2,6>undecane

: 82891-12-1
15-(tert-butyldimethylsiloxy)-4α-tosyloxytrichothecane-9,12-diene

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) sodium borohydride; 2.) chromium trioxide, pyridine / 1.) methanol, 20 min, r.t.; 2.) CH₂Cl₂, 35 min, r.t.

2: 88.7 percent / 470 °C / 1.2 - 1.5 Torr / flash vacuum thermolysis

3: 1.) lithium tetramethylpiperidine / 1.) THF, hexane, 30 min, -20 deg C, 30 min, -10 deg C, 10 min, 0 deg C; 2.) r.t. 15 min

4: pyridine; CH₂Cl₂ / 0.13 h / -78 °C

5: 1.) TFA; 2.) H₂O / 1.) r.t., ethylene dichloride; 2.) 32 deg C, 14 h, 45 deg C, 1 h, 55 deg C, 15 min

6: tetrabutylammonium fluoride / tetrahydrofuran / 1.75 h

7: 95 percent / hexane; tetrahydrofuran / 0.1 h / 60 - 62 °C

8: 95 percent / diisobutylaluminum hydride / toluene / 6.5 h / Ambient temperature

9: 85 percent / DMAP / CH₂Cl₂ / 4.5 h / 0 °C

10: 79.4 percent Turnov_. / pyridine, 60 h, 34 deg C; H₂O, 20 min 0 deg C

With pyridine; chromium(VI) oxide; dmap; sodium tetrahydroborate; 2,2,6,6-tetramethylpiperidinyl-lithium; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; trifluoroacetic acid; In tetrahydrofuran; pyridine; hexane; dichloromethane; toluene;
DOI:10.1021/ja00314a023

Reference yield:

: 82891-03-0
(3aR,4S,8R,8aR)-8a-Hydroxy-3a-methyl-7-methylene-3-oxo-9-trimethylsilanyloxy-octahydro-4,8-methano-azulene-4-carboxylic acid methyl ester

: 82891-12-1
Toluene-4-sulfonic acid (1S,2R,7R,9R,11S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-1,5-dimethyl-12-methylene-8-oxa-tricyclo[7.2.1.0^2,7]dodec-5-en-11-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) sodium borohydride, 2.) CrO₃-2pyr / 1.) MeOH, room temperature, 20 min, 2.) CH₂Cl₂, room temperature, 35 min

2: 89 percent / 470 °C / 1.2 - 1.5 Torr / hot tube, 16 cm

3: 1.) lithium tetramethylpiperidide, 2.) trimethylsilyl chloride, 3.) bromine dioxane complex

4: trifluoroacetic acid / H₂O; 1,2-dichloro-ethane / 1.) 32 deg C, 14 h, 2.) 45 deg C, 1 h, 3.) 55 deg C, 15 min

5: tetra-n-butylammonium fluoride / tetrahydrofuran

6: 95 percent / LiBr / tetrahydrofuran / 0.1 h / 60 °C

7: 95 percent / diisobutylaluminum hydride / toluene / 6.5 h / Ambient temperature

8: 82 percent / DMAP / CH₂Cl₂ / 4.5 h / 0 °C

9: 79 percent / pyridine / 60 h / 34 °C

With pyridine; dmap; sodium tetrahydroborate; chloro-trimethyl-silane; bromine dioxane; 2,2,6,6-tetramethylpiperidinyl-lithium; tetrabutyl ammonium fluoride; dipyridine chromium trioxide; diisobutylaluminium hydride; trifluoroacetic acid; lithium bromide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ja00386a044