(4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

Base Information

Chemical Name:(4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one
CAS No.:1399680-44-4
Molecular Formula:C₄₈H₇₀O₆Si₂
Molecular Weight:799.251
Hs Code.:

(4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

Synonyms:(4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

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Chemical Property of (4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

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Technology Process of (4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

There total 16 articles about (4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-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: 83.0%

: 1399679-99-2
(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

: 1399680-44-4
(4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

: 1399680-29-5
(E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; p-benzoquinone; In toluene; at 100 ℃; for 4h; Inert atmosphere;
DOI:10.1021/ol301886g

Reference yield:

: 1399680-18-2
(6R,7S)-tert-butyl 6-hydroxy-7-((4-methoxybenzyl)oxy)-3-oxonon-8-enoate

: 1399680-44-4
(4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

: 1399680-29-5
(E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1H-imidazole / dichloromethane / 4 h / 0 - 23 °C / Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran / -20 °C

3.1: 1H-imidazole; dmap / dichloromethane / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / tetrahydrofuran / 36 h / 23 °C / Inert atmosphere

5.1: tetrahydrofuran; diethyl ether / 2 h / -78 - -40 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: triethylamine / tetrahydrofuran / 0.5 h / 0 - 23 °C / Inert atmosphere

8.1: dmap / toluene / 0 - 23 °C

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 23 °C / pH 7

10.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; p-benzoquinone / toluene / 4 h / 100 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium tetrahydroborate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol301886g

Reference yield:

: 1399679-81-2
(6R,7S)-tert-butyl 7-((4-methoxybenzyl)oxy)-3-oxo-6-((triethylsilyl)oxy)non-8-enoate

: 1399680-44-4
(4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

: 1399680-29-5
(E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / -20 °C

2.1: 1H-imidazole; dmap / dichloromethane / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / tetrahydrofuran / 36 h / 23 °C / Inert atmosphere

4.1: tetrahydrofuran; diethyl ether / 2 h / -78 - -40 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: triethylamine / tetrahydrofuran / 0.5 h / 0 - 23 °C / Inert atmosphere

7.1: dmap / toluene / 0 - 23 °C

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 23 °C / pH 7

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; p-benzoquinone / toluene / 4 h / 100 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium tetrahydroborate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol301886g