(1R,2R,6R,7R)-9-<<(tert-butyl)dimethylsilyl>oxy>-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>deca-4,8-diene

Base Information

• Chemical Name: (1R,2R,6R,7R)-9-<<(tert-butyl)dimethylsilyl>oxy>-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>deca-4,8-diene
• CAS No.: 157544-85-9
• Molecular Formula: C₁₉H₂₅NO₃Si
• Molecular Weight: 343.498

Synonyms:(1R,2R,6R,7R)-9-<<(tert-butyl)dimethylsilyl>oxy>-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>deca-4,8-diene

Chemical Property of (1R,2R,6R,7R)-9-<<(tert-butyl)dimethylsilyl>oxy>-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>deca-4,8-diene

Chemical Property:

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Technology Process of (1R,2R,6R,7R)-9-<<(tert-butyl)dimethylsilyl>oxy>-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>deca-4,8-diene

There total 6 articles about (1R,2R,6R,7R)-9-<<(tert-butyl)dimethylsilyl>oxy>-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>deca-4,8-diene 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: 88.0%

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide (77377-52-7) + (1S,2R,6R,7R)-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.02,6>dec-4-en-9-one → (1R,2R,6R,7R)-9-<<(tert-butyl)dimethylsilyl>oxy>-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.02,6>deca-4,8-diene (157544-85-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 60 ℃; for 7h;

DOI:10.1016/0008-6215(94)80034-0

Reference yield:

(1R,2R,4R)-2-exo-cyano-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl(1S)-camphanate (88764-13-0) → (1R,2R,6R,7R)-9-<<(tert-butyl)dimethylsilyl>oxy>-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.02,6>deca-4,8-diene (157544-85-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) acetone, 50 deg C, 2 d, 2.) acetone, 0 deg C, 2 h, irrad.

2: 99 percent / CF₃COOH / CH₂Cl₂ / 15 h

3: 90 percent / Et₃N / CH₂Cl₂ / 15 h

4: 80 percent / CF₃SO₃H / various solvent(s) / 1 h / 80 °C

5: 93 percent / K₂CO₃, 37percent formaline / methanol / 3 h / 20 °C

6: 88 percent / Et₃N / dimethylformamide / 7 h / 60 °C

With formaldehyd; trifluorormethanesulfonic acid; potassium carbonate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(94)80034-0

Reference yield:

(1R,2S,4R,5R,6S)-<6-exo-cyano-8-oxa-3-azatricyclo<3.2.1.02,4>oct-6-endo-yl(1S)-camphanate> → (1R,2R,6R,7R)-9-<<(tert-butyl)dimethylsilyl>oxy>-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.02,6>deca-4,8-diene (157544-85-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / Et₃N / CH₂Cl₂ / 15 h

2: 80 percent / CF₃SO₃H / various solvent(s) / 1 h / 80 °C

3: 93 percent / K₂CO₃, 37percent formaline / methanol / 3 h / 20 °C

4: 88 percent / Et₃N / dimethylformamide / 7 h / 60 °C

With formaldehyd; trifluorormethanesulfonic acid; potassium carbonate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(94)80034-0

upstream raw materials:

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide

(1R,2R,4R)-2-exo-cyano-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl(1S)-camphanate

(1R,2R,6R,7R,9S)-<9-exo-cyano-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-en-2-endo-yl(1S)-camphanate>

Downstream raw materials:

methyl 3-amino-1,5-anhydro-2-O,3-N-benzoyl-3-deoxy-α-L-talofuranuronate

3-amino-1,5-anhydro-2-O,3-N-benzoyl-3-deoxy-α-L-talofuranose

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