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

Base Information

• Chemical Name: (2aR,4S,4aS,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one
• CAS No.: 168421-83-8
• Molecular Formula: C₂₅H₃₈O₄Si
• Molecular Weight: 430.66

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 15 articles about (2aR,4S,4aS,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-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: 84.0%

C27H42O5Si (168421-57-6) → (2aR,4S,4aS,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one (168421-83-8)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; at 70 ℃;

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2aR,4S,4aS,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one (168421-83-8)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; 2,6-dimethylpyridine; palladium dihydroxide; sodium hydroxide; osmium(VIII) oxide; dipyridinium dichromate; borane-THF; water; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 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)-4'a-Methyl-3',4',4'a,5',6',7'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-ol (155681-62-2) → (2aR,4S,4aS,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one (168421-83-8)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; 2,6-dimethylpyridine; palladium dihydroxide; sodium hydroxide; osmium(VIII) oxide; dipyridinium dichromate; borane-THF; water; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 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:

C₂₇H₄₂O₅Si

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

t-butyldimethylsiyl triflate

benzyl bromide

Downstream raw materials:

(2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate

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

2-[(1S,2S,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]-ethanol

(1S,2S,3S,4S,6R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-(2,2-dimethoxyethyl)-3-methyl-7-oxabicyclo[4.2.0]octane-2-carbaldehyde

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