5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone

Base Information

Chemical Name:5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone
CAS No.:168421-65-6
Molecular Formula:C₃₅H₅₄O₇Si
Molecular Weight:614.895
Hs Code.:

5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone

Synonyms:5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone

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Chemical Property of 5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone

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Technology Process of 5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone

There total 25 articles about 5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone 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:

: 878-47-7,4242-00-6,34996-06-0,50302-16-4,70191-02-5,34996-05-9
(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one

: 168421-65-6
5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone

Guidance literature:: Multi-step reaction with 21 steps

1: 1.) Ac₂O, DMAP, Py, 2.) naphthalenesulfonic acid, 3.) NaOMe

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

3: 1.) BH₃*THF, 2.) aq. H₂O₂, aq. NaOH, 3.) pyridinium dichromate

4: 1.) KHMDS / 1.) THF, -78 deg C, 2.) THF

5: 73 percent / Pd(OH)2, Ph₃P, Hunig's base / dimethylformamide

6: 99 percent / DIBAL / hexane / -78 °C

7: 45 percent / N-methylmorpholine N-oxide monohydrate (NMO), OsO₄, H₂O / acetone; propan-2-ol / 15 h / Ambient temperature

8: Py / CH₂Cl₂ / 3 h / Ambient temperature

9: CH₂Cl₂ / 1.5 h / Ambient temperature

10: ethane-1,2-diol; CH₂Cl₂ / 14.5 h / Heating

11: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 0 deg C 0.5 h, 2.) THF, RT, 4 h

12: 84 percent / TsOH / acetone; H₂O / 2.5 h / Heating

13: 84 percent / Et₃N / CH₂Cl₂; H₂O / 4 h / -78 °C / Heating

14: 1.) 3,3-dimethyldioxirane, 2.) camphorosulfonic acid / 1.) CH₂Cl₂, Me₂CO, 10 min, 2.) Me₂CO, 0.5 h

15: 97 percent / Pb(OAc)4 / benzene / 0.17 h / 0 °C

16: 97 percent / collidinium p-toluene sulfonate (CPTS) / 10 h / Heating

17: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

18: 88 percent / Bu₃P / tetrahydrofuran / 0.25 h / Ambient temperature

19: 90 percent / aq. H₂O₂ / tetrahydrofuran / 12 h / Ambient temperature

20: 1.) O₃, NaHCO₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 0.5 h

21: 1.) tBuLi, 3.) tetrabutylammonium fluoride

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; dmap; palladium dihydroxide; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; borane-THF; tributylphosphine; collidinium p-toluene sulfonate; naphthalenesulfonic acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; tert.-butyl lithium; sodium methylate; 3,3-dimethyldioxirane; acetic anhydride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol; acetone; benzene;
DOI:10.1021/ja952692a

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 168421-65-6
5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone

Guidance literature:: Multi-step reaction with 20 steps

1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 1.) BH₃*THF, 2.) aq. H₂O₂, aq. NaOH, 3.) pyridinium dichromate

3: 1.) KHMDS / 1.) THF, -78 deg C, 2.) THF

4: 73 percent / Pd(OH)2, Ph₃P, Hunig's base / dimethylformamide

5: 99 percent / DIBAL / hexane / -78 °C

6: 45 percent / N-methylmorpholine N-oxide monohydrate (NMO), OsO₄, H₂O / acetone; propan-2-ol / 15 h / Ambient temperature

7: Py / CH₂Cl₂ / 3 h / Ambient temperature

8: CH₂Cl₂ / 1.5 h / Ambient temperature

9: ethane-1,2-diol; CH₂Cl₂ / 14.5 h / Heating

10: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 0 deg C 0.5 h, 2.) THF, RT, 4 h

11: 84 percent / TsOH / acetone; H₂O / 2.5 h / Heating

12: 84 percent / Et₃N / CH₂Cl₂; H₂O / 4 h / -78 °C / Heating

13: 1.) 3,3-dimethyldioxirane, 2.) camphorosulfonic acid / 1.) CH₂Cl₂, Me₂CO, 10 min, 2.) Me₂CO, 0.5 h

14: 97 percent / Pb(OAc)4 / benzene / 0.17 h / 0 °C

15: 97 percent / collidinium p-toluene sulfonate (CPTS) / 10 h / Heating

16: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

17: 88 percent / Bu₃P / tetrahydrofuran / 0.25 h / Ambient temperature

18: 90 percent / aq. H₂O₂ / tetrahydrofuran / 12 h / Ambient temperature

19: 1.) O₃, NaHCO₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 0.5 h

20: 1.) tBuLi, 3.) tetrabutylammonium fluoride

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; palladium dihydroxide; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; borane-THF; tributylphosphine; collidinium p-toluene sulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; tert.-butyl lithium; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol; acetone; benzene;
DOI:10.1021/ja952692a

Reference yield:

: 155681-64-4
(4'aS,5'S,8'aS)-5'-(tert-Butyl-dimethyl-silanyloxy)-4'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-one

: 168421-65-6
5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone

Guidance literature:: Multi-step reaction with 18 steps

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

2: 73 percent / Pd(OH)2, Ph₃P, Hunig's base / dimethylformamide

3: 99 percent / DIBAL / hexane / -78 °C

4: 45 percent / N-methylmorpholine N-oxide monohydrate (NMO), OsO₄, H₂O / acetone; propan-2-ol / 15 h / Ambient temperature

5: Py / CH₂Cl₂ / 3 h / Ambient temperature

6: CH₂Cl₂ / 1.5 h / Ambient temperature

7: ethane-1,2-diol; CH₂Cl₂ / 14.5 h / Heating

8: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 0 deg C 0.5 h, 2.) THF, RT, 4 h

9: 84 percent / TsOH / acetone; H₂O / 2.5 h / Heating

10: 84 percent / Et₃N / CH₂Cl₂; H₂O / 4 h / -78 °C / Heating

11: 1.) 3,3-dimethyldioxirane, 2.) camphorosulfonic acid / 1.) CH₂Cl₂, Me₂CO, 10 min, 2.) Me₂CO, 0.5 h

12: 97 percent / Pb(OAc)4 / benzene / 0.17 h / 0 °C

13: 97 percent / collidinium p-toluene sulfonate (CPTS) / 10 h / Heating

14: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

15: 88 percent / Bu₃P / tetrahydrofuran / 0.25 h / Ambient temperature

16: 90 percent / aq. H₂O₂ / tetrahydrofuran / 12 h / Ambient temperature

17: 1.) O₃, NaHCO₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 0.5 h

18: 1.) tBuLi, 3.) tetrabutylammonium fluoride

With pyridine; lead(IV) acetate; palladium dihydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; tributylphosphine; collidinium p-toluene sulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; tert.-butyl lithium; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol; acetone; benzene;
DOI:10.1021/ja952692a