(E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1⁽¹⁹⁾,9,16⁽²⁰⁾,17-tetraen-15-one

Base Information

• Chemical Name: (E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1⁽¹⁹⁾,9,16⁽²⁰⁾,17-tetraen-15-one
• CAS No.: 211692-08-9
• Molecular Formula: C₂₅H₂₈O₅
• Molecular Weight: 408.494

Synonyms:(E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1⁽¹⁹⁾,9,16⁽²⁰⁾,17-tetraen-15-one

Chemical Property of (E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1⁽¹⁹⁾,9,16⁽²⁰⁾,17-tetraen-15-one

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Technology Process of (E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1⁽¹⁹⁾,9,16⁽²⁰⁾,17-tetraen-15-one

There total 4 articles about (E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1⁽¹⁹⁾,9,16⁽²⁰⁾,17-tetraen-15-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:

methyl 4-formylbenzoate (1571-08-0) → (E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.12,5]henicosa-1(19),9,16(20),17-tetraen-15-one (211692-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: TsOH, molecular sieves 4 Angstroem

2: H₂O, LiOH / methanol; tetrahydrofuran

3: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 2 h, 2.) THF, toluene, reflux, 20 h

With dmap; lithium hydroxide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; water; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U

Reference yield:

Benzoic acid (E)-(8S,9R)-8-benzyloxy-9,10-dihydroxy-dec-4-enyl ester (211691-90-6) → (E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.12,5]henicosa-1(19),9,16(20),17-tetraen-15-one (211692-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: TsOH, molecular sieves 4 Angstroem

2: H₂O, LiOH / methanol; tetrahydrofuran

3: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 2 h, 2.) THF, toluene, reflux, 20 h

With dmap; lithium hydroxide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; water; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U

Reference yield:

4-[(2S,4R)-4-((E)-(S)-8-Benzoyloxy-1-benzyloxy-oct-4-enyl)-[1,3]dioxolan-2-yl]-benzoic acid methyl ester → (E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.12,5]henicosa-1(19),9,16(20),17-tetraen-15-one (211692-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O, LiOH / methanol; tetrahydrofuran

2: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 2 h, 2.) THF, toluene, reflux, 20 h

With dmap; lithium hydroxide; 2,4,6-trichlorobenzoyl chloride; water; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U

upstream raw materials:

4-[(2S,4R)-4-((E)-(S)-1-Benzyloxy-8-hydroxy-oct-4-enyl)-[1,3]dioxolan-2-yl]-benzoic acid

methyl 4-formylbenzoate

Benzoic acid (E)-(8S,9R)-8-benzyloxy-9,10-dihydroxy-dec-4-enyl ester

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