(2S,5S,6R,7R,9S,10R)-6-Benzyloxy-2-ethyl-1-hydroxy-5,7,9-trimethyl-3,13-dioxa-bicyclo[8.2.1]tridec-11-en-4-one

Base Information

Chemical Name:(2S,5S,6R,7R,9S,10R)-6-Benzyloxy-2-ethyl-1-hydroxy-5,7,9-trimethyl-3,13-dioxa-bicyclo[8.2.1]tridec-11-en-4-one
CAS No.:123488-88-0
Molecular Formula:C₂₃H₃₂O₅
Molecular Weight:388.504
Hs Code.:

Synonyms:(2S,5S,6R,7R,9S,10R)-6-Benzyloxy-2-ethyl-1-hydroxy-5,7,9-trimethyl-3,13-dioxa-bicyclo[8.2.1]tridec-11-en-4-one

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Chemical Property of (2S,5S,6R,7R,9S,10R)-6-Benzyloxy-2-ethyl-1-hydroxy-5,7,9-trimethyl-3,13-dioxa-bicyclo[8.2.1]tridec-11-en-4-one

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Technology Process of (2S,5S,6R,7R,9S,10R)-6-Benzyloxy-2-ethyl-1-hydroxy-5,7,9-trimethyl-3,13-dioxa-bicyclo[8.2.1]tridec-11-en-4-one

There total 14 articles about (2S,5S,6R,7R,9S,10R)-6-Benzyloxy-2-ethyl-1-hydroxy-5,7,9-trimethyl-3,13-dioxa-bicyclo[8.2.1]tridec-11-en-4-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:

: 110314-26-6,123538-63-6
1-((E)-(2R,6R,8S,9S,10R)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundec-4-en-2-yl)-propan-1-one

: 123488-88-0
(2S,5S,6R,7R,9S,10R)-6-Benzyloxy-2-ethyl-1-hydroxy-5,7,9-trimethyl-3,13-dioxa-bicyclo[8.2.1]tridec-11-en-4-one

Guidance literature:: Multi-step reaction with 13 steps

1: 94.2 percent / LiHBEt₃ / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) room temp., 0.5 h

2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3: 99 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1.) -78 deg C, 3 h, 2.) -40 h, 1 h

4: 1.) n-BuLi, 1,10-phenanthroline / 1.) THF, -78 deg C, 1 h, 2.) 15 min

5: iodine / tetrahydrofuran; CH₂Cl₂ / 3 h / 0 °C

7: 100 percent / 48percent HF / acetonitrile / 1.75 h

8: 63 percent / camphorsulfonic acid / benzene / 72 h / 70 °C

9: 87 percent / 2,6-lutidine / acetonitrile; CH₂Cl₂ / 2 h / 0 °C

10: benzene / 0.67 h / Irradiation

11: Bu₄NF / tetrahydrofuran / 0.33 h / -18 °C

12: 80 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 24 h / Ambient temperature

13: diazabicyclononane / CH₂Cl₂ / 3 h

With 2,6-dimethylpyridine; n-butyllithium; 1,10-Phenanthroline; diazabicyclononane; camphor-10-sulfonic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; iodine; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ja00204a016

Reference yield:

: 110314-27-7,110351-98-9
(R)-1-((E)-(2R,6R,8S,9S,10R)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundec-4-en-2-yl)-propan-1-ol

: 123488-88-0
(2S,5S,6R,7R,9S,10R)-6-Benzyloxy-2-ethyl-1-hydroxy-5,7,9-trimethyl-3,13-dioxa-bicyclo[8.2.1]tridec-11-en-4-one

Guidance literature:: Multi-step reaction with 12 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2: 99 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1.) -78 deg C, 3 h, 2.) -40 h, 1 h

3: 1.) n-BuLi, 1,10-phenanthroline / 1.) THF, -78 deg C, 1 h, 2.) 15 min

4: iodine / tetrahydrofuran; CH₂Cl₂ / 3 h / 0 °C

6: 100 percent / 48percent HF / acetonitrile / 1.75 h

7: 63 percent / camphorsulfonic acid / benzene / 72 h / 70 °C

8: 87 percent / 2,6-lutidine / acetonitrile; CH₂Cl₂ / 2 h / 0 °C

9: benzene / 0.67 h / Irradiation

10: Bu₄NF / tetrahydrofuran / 0.33 h / -18 °C

11: 80 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 24 h / Ambient temperature

12: diazabicyclononane / CH₂Cl₂ / 3 h

With 2,6-dimethylpyridine; n-butyllithium; 1,10-Phenanthroline; diazabicyclononane; camphor-10-sulfonic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; iodine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ja00204a016

Reference yield:

: 110314-26-6,123538-63-6
1-((E)-(2S,6R,8S,9S,10R)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundec-4-en-2-yl)-propan-1-one

: 123488-88-0
(2S,5S,6R,7R,9S,10R)-6-Benzyloxy-2-ethyl-1-hydroxy-5,7,9-trimethyl-3,13-dioxa-bicyclo[8.2.1]tridec-11-en-4-one

Guidance literature:: Multi-step reaction with 13 steps

1: 4.6 percent / LiHBEt₃ / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) room temp., 0.5 h

2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3: 99 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1.) -78 deg C, 3 h, 2.) -40 h, 1 h

4: 1.) n-BuLi, 1,10-phenanthroline / 1.) THF, -78 deg C, 1 h, 2.) 15 min

5: iodine / tetrahydrofuran; CH₂Cl₂ / 3 h / 0 °C

7: 100 percent / 48percent HF / acetonitrile / 1.75 h

8: 63 percent / camphorsulfonic acid / benzene / 72 h / 70 °C

9: 87 percent / 2,6-lutidine / acetonitrile; CH₂Cl₂ / 2 h / 0 °C

10: benzene / 0.67 h / Irradiation

11: Bu₄NF / tetrahydrofuran / 0.33 h / -18 °C

12: 80 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 24 h / Ambient temperature

13: diazabicyclononane / CH₂Cl₂ / 3 h

With 2,6-dimethylpyridine; n-butyllithium; 1,10-Phenanthroline; diazabicyclononane; camphor-10-sulfonic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; iodine; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ja00204a016