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

Base Information

Chemical Name:(E)-(3R,4S,5S,7R,8S,12R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-12-ethyl-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione
CAS No.:123538-78-3
Molecular Formula:C₂₉H₄₆O₅Si
Molecular Weight:502.767
Hs Code.:

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

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

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

There total 18 articles about (E)-(3R,4S,5S,7R,8S,12R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-12-ethyl-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: 100.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

: 123538-78-3
(E)-(3R,4S,5S,7R,8S,12R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-12-ethyl-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1021/ja00204a016

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

: 123538-78-3
(E)-(3R,4S,5S,7R,8S,12R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-12-ethyl-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione

Guidance literature:: Multi-step reaction with 7 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

7: 2,6-lutidine

With 2,6-dimethylpyridine; 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

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

: 123538-78-3
(E)-(3R,4S,5S,7R,8S,12R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-12-ethyl-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione

Guidance literature:: Multi-step reaction with 10 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

10: 2,6-lutidine

With 2,6-dimethylpyridine; 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