(4S,14S)-4,14-Diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17-diene-19,21-dione

Base Information

• Chemical Name: (4S,14S)-4,14-Diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17-diene-19,21-dione
• CAS No.: 189451-80-7
• Molecular Formula: C₂₈H₃₀O₇
• Molecular Weight: 478.542

Synonyms:(4S,14S)-4,14-Diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17-diene-19,21-dione

Chemical Property of (4S,14S)-4,14-Diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17-diene-19,21-dione

Chemical Property:

Purity/Quality:

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Technology Process of (4S,14S)-4,14-Diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17-diene-19,21-dione

There total 5 articles about (4S,14S)-4,14-Diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17-diene-19,21-dione 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: 98.0%

(4S,14S)-19-Methoxy-4,14-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol (189451-76-1) → (4S,14S)-4,14-Diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17-diene-19,21-dione (189451-80-7)

Guidance literature:

With ammonium cerium(IV) nitrate; In acetonitrile; for 0.5h; Ambient temperature;

DOI:10.1016/S0957-4166(97)00047-5

Reference yield:

1,3-bis-bromomethyl-2,5-dimethoxy-benzene (72652-35-8) → (4S,14S)-4,14-Diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17-diene-19,21-dione (189451-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / NaH, KBF₄ / tetrahydrofuran / 29 h / Heating

2: 74 percent / ethanethiol, NaH / dimethylformamide / 3 h / 100 °C

3: 98 percent / CAN / acetonitrile / 0.5 h / Ambient temperature

With ammonium cerium(IV) nitrate; sodium hydride; potassium tetrafluoroborate; ethanethiol; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0957-4166(97)00047-5

Reference yield:

(S,S)-(+)-1,11-diphenyl-3,6,9-trioxaundecane-1,11-diol (93417-23-3) → (4S,14S)-4,14-Diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17-diene-19,21-dione (189451-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / NaH, KBF₄ / tetrahydrofuran / 29 h / Heating

2: 74 percent / ethanethiol, NaH / dimethylformamide / 3 h / 100 °C

3: 98 percent / CAN / acetonitrile / 0.5 h / Ambient temperature

With ammonium cerium(IV) nitrate; sodium hydride; potassium tetrafluoroborate; ethanethiol; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0957-4166(97)00047-5

upstream raw materials:

(4S,14S)-19-Methoxy-4,14-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17⁽²¹⁾,18-trien-21-ol

1,3-bis-bromomethyl-2,5-dimethoxy-benzene

(S,S)-(+)-1,11-diphenyl-3,6,9-trioxaundecane-1,11-diol

(4S,14S)-19,21-Dimethoxy-4,14-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17⁽²¹⁾,18-triene

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