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

Base Information

• Chemical Name: 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.0^3,7]dodecan-8-one
• CAS No.: 925545-61-5
• Molecular Formula: C₂₄H₂₇NO₅
• Molecular Weight: 409.482

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

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

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

There total 22 articles about 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.0^3,7]dodecan-8-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: 100.0%

11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.03,7]dodecan-8-ol (925545-60-4) → 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.03,7]dodecan-8-one (925545-61-5)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; at 20 ℃; for 36h;

DOI:10.1021/ol062621o

Reference yield: 91.0%

11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.03,7]dodecan-8-ol → 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.03,7]dodecan-8-one (925545-61-5)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; at 20 ℃; for 36h;

DOI:10.1021/ol062621o

Reference yield:

D-xylose (58-86-6) → 11-benzyl-2-benzyloxy-5,5-dimethyl-4,6,10-trioxa-11-aza-tricyclo[7.2.1.03,7]dodecan-8-one (925545-61-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: p-TsOH / 12 h / 0 °C

2.1: magnesium / tetrahydrofuran

2.2: 348 mg / tetrahydrofuran / 13.5 h / -78 - 20 °C

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

4.1: 535 mg / AcOH / H₂O / 11 h / 20 °C

5.1: imidazole / CH₂Cl₂ / 2 h / 20 °C

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

7.1: 324 mg / TBAF / tetrahydrofuran / 3 h / 20 °C

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

9.1: CH₂Cl₂ / 1 h / 20 °C

10.1: 83.1 mg / triethylamine / acetonitrile / 2 h / Heating

11.1: potassium carbonate / methanol; CH₂Cl₂ / 6 h / 20 °C

12.1: 100 percent / IBX / CH₂Cl₂; dimethylsulfoxide / 36 h / 20 °C

With pyridine; 1H-imidazole; dmap; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; magnesium; 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

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

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

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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