methanesulfonic acid 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.0^3,7]dodec-8-yl ester

Base Information

• Chemical Name: methanesulfonic acid 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.0^3,7]dodec-8-yl ester
• CAS No.: 925545-65-9
• Molecular Formula: C₂₅H₃₁NO₇S
• Molecular Weight: 489.59

Synonyms:methanesulfonic acid 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.0^3,7]dodec-8-yl ester

Chemical Property of methanesulfonic acid 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.0^3,7]dodec-8-yl ester

Chemical Property:

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Technology Process of methanesulfonic acid 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.0^3,7]dodec-8-yl ester

There total 12 articles about methanesulfonic acid 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.0^3,7]dodec-8-yl ester 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: 100.0%

11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.03,7]dodecan-8-ol (925545-64-8) + methanesulfonyl chloride (124-63-0) → methanesulfonic acid 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.03,7]dodec-8-yl ester (925545-65-9)

Guidance literature:

With dmap; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol062621o

Reference yield:

1-(2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-prop-2-en-1-ol (881302-88-1) → methanesulfonic acid 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.03,7]dodec-8-yl ester (925545-65-9)

Guidance literature:

Multi-step reaction with 10 steps

1: pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

2: 1.15 g / AcOH / H₂O / 10 h / 20 °C

3: imidazole / CH₂Cl₂ / 2 h / 20 °C

4: trifluoromethanesulfonic acid / cyclohexane; CH₂Cl₂ / 3.5 h / 0 - 20 °C

5: 1.82 g / TBAF / tetrahydrofuran / 3 h / 20 °C

6: IBX / dimethylsulfoxide; CH₂Cl₂ / 12 h / 20 °C

7: CH₂Cl₂ / 1 h / 20 °C

8: 16.3 mg / triethylamine / acetonitrile / 2 h / Heating

9: 100 percent / potassium carbonate / methanol; CH₂Cl₂ / 8 h / 20 °C

10: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; dmap; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/ol062621o

Reference yield:

benzoic acid 1-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester (925545-44-4) → methanesulfonic acid 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.03,7]dodec-8-yl ester (925545-65-9)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / CH₂Cl₂ / 2 h / 20 °C

2: trifluoromethanesulfonic acid / cyclohexane; CH₂Cl₂ / 3.5 h / 0 - 20 °C

3: 1.82 g / TBAF / tetrahydrofuran / 3 h / 20 °C

4: IBX / dimethylsulfoxide; CH₂Cl₂ / 12 h / 20 °C

5: CH₂Cl₂ / 1 h / 20 °C

6: 16.3 mg / triethylamine / acetonitrile / 2 h / Heating

7: 100 percent / potassium carbonate / methanol; CH₂Cl₂ / 8 h / 20 °C

8: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; dmap; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/ol062621o

upstream raw materials:

11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.0^3,7]dodecan-8-ol

methanesulfonyl chloride

1-(2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-prop-2-en-1-ol

benzoic acid 1-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester

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