(1S,4S,5R,6R)-6-Benzyloxy-4-(tert-butyldimethylsilyloxy)-4-(prop-2-enyl)-2-oxabicyclo<3.2.1>octan-3-one

Base Information

• Chemical Name: (1S,4S,5R,6R)-6-Benzyloxy-4-(tert-butyldimethylsilyloxy)-4-(prop-2-enyl)-2-oxabicyclo<3.2.1>octan-3-one
• CAS No.: 130504-30-2
• Molecular Formula: C₂₃H₃₄O₄Si
• Molecular Weight: 402.606
• Mol file: 130504-30-2.mol

Synonyms:

Chemical Property of (1S,4S,5R,6R)-6-Benzyloxy-4-(tert-butyldimethylsilyloxy)-4-(prop-2-enyl)-2-oxabicyclo<3.2.1>octan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,5R,6R)-6-Benzyloxy-4-(tert-butyldimethylsilyloxy)-4-(prop-2-enyl)-2-oxabicyclo<3.2.1>octan-3-one

There total 16 articles about (1S,4S,5R,6R)-6-Benzyloxy-4-(tert-butyldimethylsilyloxy)-4-(prop-2-enyl)-2-oxabicyclo<3.2.1>octan-3-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:

(1S,4S,5S)-5-Bromobicyclo<2.2.1>heptan-2-one (128111-35-3) → (1S,4S,5R,6R)-6-Benzyloxy-4-(tert-butyldimethylsilyloxy)-4-(prop-2-enyl)-2-oxabicyclo<3.2.1>octan-3-one (130504-30-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / pyridinium p-toluenesulphonate / benzene / 3 h / Heating

2: 81 percent / potassium superoxide, 18-crown-6 / dimethylsulfoxide; 1,2-dimethoxy-ethane / 60 h / Ambient temperature; repeated addition of K₂O and 18-crown-6

3: 1.) sodium hydride, 2.) tetra-n-butylammonium iodide / 1.) THF, r.t., 30 min, 2.) r.t., 12 h

4: 1 M HCl / tetrahydrofuran / 2.75 h / 50 °C

5: 91 percent / m-chloroperbenzoic acid, p-toluenesulphonic acid monohydrate / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) lithium diisopropylamide, 2.) oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 15 min, then -30 to -20 deg C, 30 min, then to r.t.

7: imidazole / dimethylformamide / 14 h / Ambient temperature

8: 1a.) potassium diisopropylamide, 1b.) HMPA / 1.) THF, hexane, -78 deg C, 2.) -78 to 0 deg C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium superoxide; 18-crown-6 ether; oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium diisopropylamide; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)82332-2

Reference yield:

benzyl bromide (100-39-0) → (1S,4S,5R,6R)-6-Benzyloxy-4-(tert-butyldimethylsilyloxy)-4-(prop-2-enyl)-2-oxabicyclo<3.2.1>octan-3-one (130504-30-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) sodium hydride, 2.) tetra-n-butylammonium iodide / 1.) THF, r.t., 30 min, 2.) r.t., 12 h

2: 1 M HCl / tetrahydrofuran / 2.75 h / 50 °C

3: 91 percent / m-chloroperbenzoic acid, p-toluenesulphonic acid monohydrate / CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) lithium diisopropylamide, 2.) oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 15 min, then -30 to -20 deg C, 30 min, then to r.t.

5: imidazole / dimethylformamide / 14 h / Ambient temperature

6: 1a.) potassium diisopropylamide, 1b.) HMPA / 1.) THF, hexane, -78 deg C, 2.) -78 to 0 deg C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium diisopropyl amide; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)82332-2

Reference yield:

(1S,2S,4S,5S)-5-Bromobicyclo<2.2.1>heptan-2-ol (138125-10-7) → (1S,4S,5R,6R)-6-Benzyloxy-4-(tert-butyldimethylsilyloxy)-4-(prop-2-enyl)-2-oxabicyclo<3.2.1>octan-3-one (130504-30-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 83 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine-N-oxide, 4 Angstroem molecular sieves / acetonitrile / 12 h / Ambient temperature

2: 92 percent / pyridinium p-toluenesulphonate / benzene / 3 h / Heating

3: 81 percent / potassium superoxide, 18-crown-6 / dimethylsulfoxide; 1,2-dimethoxy-ethane / 60 h / Ambient temperature; repeated addition of K₂O and 18-crown-6

4: 1.) sodium hydride, 2.) tetra-n-butylammonium iodide / 1.) THF, r.t., 30 min, 2.) r.t., 12 h

5: 1 M HCl / tetrahydrofuran / 2.75 h / 50 °C

6: 91 percent / m-chloroperbenzoic acid, p-toluenesulphonic acid monohydrate / CH₂Cl₂ / 1 h / Ambient temperature

7: 1.) lithium diisopropylamide, 2.) oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 15 min, then -30 to -20 deg C, 30 min, then to r.t.

8: imidazole / dimethylformamide / 14 h / Ambient temperature

9: 1a.) potassium diisopropylamide, 1b.) HMPA / 1.) THF, hexane, -78 deg C, 2.) -78 to 0 deg C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium superoxide; tetrapropylammonium perruthennate; 18-crown-6 ether; oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4 A molecular sieve; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium diisopropylamide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)82332-2

upstream raw materials:

(1R,5S,6R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-oxa-bicyclo[3.2.1]octan-3-one

allyl bromide

(1S,4S,5R)-5-hydroxybicyclo<2.2.1>heptane-2-one

(1R,5R,6R)-6-Benzyloxy-2-oxa-bicyclo[3.2.1]octan-3-one

Downstream raw materials:

(1S,3R,5RS,7S,8R,9R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.0^3,7>undecan-9-ol methanesulphonate

(1S,3R,5RS,7S,8R,9R)-9-Benzyloxy-7-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dioxatricyclo<6.2.1.0^3,7>undecane

(1S,3R,5RS,7S,8R,9S,11S)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4,10-trioxatetracyclo<6.3.1.0^3,7.0^9,11>dodecane

(1S,3R,5RS,7S,8R)-7-(tert-Butyldimethylsilyloxy)-5-phenylseleno-2,4-dioxatricyclo<6.2.1.0^3,7>undec-9-ene