(E)-(3S,4R,5R,7S,8R,12S)-4-Benzyloxy-12-ethyl-8-hydroxy-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione

Base Information

Chemical Name:(E)-(3S,4R,5R,7S,8R,12S)-4-Benzyloxy-12-ethyl-8-hydroxy-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione
CAS No.:110314-36-8
Molecular Formula:C₂₃H₃₂O₅
Molecular Weight:388.504
Hs Code.:

Synonyms:(E)-(3S,4R,5R,7S,8R,12S)-4-Benzyloxy-12-ethyl-8-hydroxy-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione

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Chemical Property of (E)-(3S,4R,5R,7S,8R,12S)-4-Benzyloxy-12-ethyl-8-hydroxy-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione

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Technology Process of (E)-(3S,4R,5R,7S,8R,12S)-4-Benzyloxy-12-ethyl-8-hydroxy-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione

There total 17 articles about (E)-(3S,4R,5R,7S,8R,12S)-4-Benzyloxy-12-ethyl-8-hydroxy-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-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: 70.0%

: (1S,4R,7R,8S,9S,11R,12S)-8-Benzyloxy-4-ethyl-7,9,11-trimethyl-5,13-dioxa-bicyclo[10.1.0]tridecane-3,6-dione

: 110314-36-8
(E)-(3S,4R,5R,7S,8R,12S)-4-Benzyloxy-12-ethyl-8-hydroxy-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene;
DOI:10.1021/ja00253a066

Reference yield:

: 110314-28-8,123538-64-7,123538-69-2,123618-31-5
[(R)-1-((E)-(2R,6R,8S,9S,10R)-9-Benzyloxy-6,8,10-trimethyl-1-oxo-1λ⁴-thia-cycloundec-4-en-2-yl)-propoxy]-tert-butyl-dimethyl-silane

: 110314-36-8
(E)-(3S,4R,5R,7S,8R,12S)-4-Benzyloxy-12-ethyl-8-hydroxy-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) BuLi

2: I₂

4: HF / H₂O; acetonitrile

5: 63 percent / camphorsulfonic acid / 70 °C

7: 1.) tert-butyldimethylsilyl nitrate ester of nitroethane / 1.) irradiation

8: 80 percent / MCPBA

9: 70 percent / DBU

With n-butyllithium; tert-butyldimethylsilyl nitrate ester of nitroethane; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; camphor-10-sulfonic acid; iodine; In water; acetonitrile;
DOI:10.1021/ja00253a066

Reference yield:

: 110314-30-2,123538-70-5
(E)-(3R,4S,5S,7R,11R)-4-Benzyloxy-11-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-propyl]-3,5,7-trimethyl-thiacycloundec-8-en-2-one

: 110314-36-8
(E)-(3S,4R,5R,7S,8R,12S)-4-Benzyloxy-12-ethyl-8-hydroxy-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione

Guidance literature:: Multi-step reaction with 6 steps

1: HF / H₂O; acetonitrile

2: 63 percent / camphorsulfonic acid / 70 °C

4: 1.) tert-butyldimethylsilyl nitrate ester of nitroethane / 1.) irradiation

5: 80 percent / MCPBA

6: 70 percent / DBU

With tert-butyldimethylsilyl nitrate ester of nitroethane; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; camphor-10-sulfonic acid; In water; acetonitrile;
DOI:10.1021/ja00253a066