(2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one

Base Information

• Chemical Name: (2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one
• CAS No.: 174589-62-9
• Molecular Formula: C₂₅H₃₈O₅Si
• Molecular Weight: 446.659

Synonyms:(2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one

Chemical Property of (2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one

There total 17 articles about (2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-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:

t-butyldimethylsiyl triflate (69739-34-0) → (2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one (174589-62-9)

Guidance literature:

Multi-step reaction with 13 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

With pyridine; 2,6-dimethylpyridine; palladium dihydroxide; sodium hydroxide; osmium(VIII) oxide; dipyridinium dichromate; borane-THF; camphor-10-sulfonic acid; water; dihydrogen peroxide; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol; acetone;

DOI:10.1021/ja952692a

Reference yield:

(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one (878-47-7,4242-00-6,34996-06-0,50302-16-4,70191-02-5,34996-05-9) → (2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one (174589-62-9)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; 2,6-dimethylpyridine; dmap; palladium dihydroxide; sodium hydroxide; osmium(VIII) oxide; dipyridinium dichromate; borane-THF; naphthalenesulfonic acid; camphor-10-sulfonic acid; water; dihydrogen peroxide; sodium methylate; 3,3-dimethyldioxirane; acetic anhydride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol; acetone;

DOI:10.1021/ja952692a

Reference yield:

(4'aS,5'S,8'aS)-5'-(tert-Butyl-dimethyl-silanyloxy)-4'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-one (155681-64-4) → (2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one (174589-62-9)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; palladium dihydroxide; osmium(VIII) oxide; camphor-10-sulfonic acid; water; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol; acetone;

DOI:10.1021/ja952692a

upstream raw materials:

(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one

t-butyldimethylsiyl triflate

benzyl bromide

C₂₀H₃₆O₅Si

Downstream raw materials:

C₃₅H₅₀O₉Si

(1S,6S)-1-{(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}-2,2,4-trimethyl-7-oxa-bicyclo[4.1.0]hept-4-en-3-one

{(1S,2S,3S,4S,6R)-1-Benzyloxy-3-(2,2-dimethoxy-ethyl)-3-methyl-2-[2-(2-nitro-phenylselanyl)-ethyl]-7-oxa-bicyclo[4.2.0]oct-4-yloxy}-tert-butyl-dimethyl-silane

Trifluoro-methanesulfonic acid (4S,5S)-4-[(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]-6,6,8-trimethyl-2-oxo-1,3-dioxa-spiro[4.5]dec-7-en-7-yl ester

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