(4S,14S)-(+)-19-benzyloxy-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene

Base Information

• Chemical Name: (4S,14S)-(+)-19-benzyloxy-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene
• CAS No.: 260967-75-7
• Molecular Formula: C₂₄H₃₃NO₆
• Molecular Weight: 431.529

Synonyms:(4S,14S)-(+)-19-benzyloxy-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene

Chemical Property of (4S,14S)-(+)-19-benzyloxy-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene

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Technology Process of (4S,14S)-(+)-19-benzyloxy-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene

There total 2 articles about (4S,14S)-(+)-19-benzyloxy-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene 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: 34.2%

(2S,12S)-2,12-dimethyl-4,7,10-trioxatridecane-2,12-diol (76946-26-4) + 4-benzyloxy-2,6-pyridinedimethanol ditosylate (249296-17-1) → (4S,14S)-(+)-19-benzyloxy-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-triene (260967-75-7)

Guidance literature:

(2S,12S)-2,12-dimethyl-4,7,10-trioxatridecane-2,12-diol; With sodium hydride; In tetrahydrofuran; 1.) 0 deg C, 10 min, 2.) RT, 30 min, 3.) reflux, 4 h;

4-benzyloxy-2,6-pyridinedimethanol ditosylate; In tetrahydrofuran; at 20 ℃; for 168000h;

DOI:10.1016/S0957-4166(99)00515-7

Reference yield:

(2S,12S)-2,12-bis(tetrahydropyranyloxy)-2,12-dimethyl-4,7,10-trioxatridecane-2,12-diol (76984-82-2) → (4S,14S)-(+)-19-benzyloxy-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-triene (260967-75-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / acidic ion-exchange resin / methanol / 18 h / 20 °C

2.1: NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) RT, 30 min, 3.) reflux, 4 h

2.2: 34.2 percent / tetrahydrofuran / 168000 h / 20 °C

With acidic ion-exchange resin; sodium hydride; In tetrahydrofuran; methanol; 1.1: Hydrolysis / 2.1: Metallation / 2.2: Condensation;

DOI:10.1016/S0957-4166(99)00515-7

Reference yield:

(4S,14S)-(+)-19-benzyloxy-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-triene (260967-75-7) → (4S,14S)-(+)-19-[(3-trityloxy)propyloxy]-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-triene (260967-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / H₂ / 10 percent Pd/C / methanol / 0.08 h

2: 85 percent / K₂CO₃ / dimethylformamide / 24 h / 100 °C

With hydrogen; potassium carbonate; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; 1: Hydrogenation / 2: Condensation;

DOI:10.1016/S0957-4166(99)00515-7

upstream raw materials:

(2S,12S)-2,12-dimethyl-4,7,10-trioxatridecane-2,12-diol

4-benzyloxy-2,6-pyridinedimethanol ditosylate

(2S,12S)-2,12-bis(tetrahydropyranyloxy)-2,12-dimethyl-4,7,10-trioxatridecane-2,12-diol

Downstream raw materials:

(4S,14S)-(+)-19-[(3-trityloxy)propyloxy]-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene

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