(E)-10-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-12-oxo-7-((triethylsilyl)oxy)-2-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-4-en-6-yl acetate

Base Information

Chemical Name:(E)-10-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-12-oxo-7-((triethylsilyl)oxy)-2-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-4-en-6-yl acetate
CAS No.:1399680-03-5
Molecular Formula:C₅₀H₇₂O₇Si₂
Molecular Weight:841.288
Hs Code.:

(E)-10-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-12-oxo-7-((triethylsilyl)oxy)-2-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-4-en-6-yl acetate

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Chemical Property of (E)-10-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-12-oxo-7-((triethylsilyl)oxy)-2-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-4-en-6-yl acetate

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Technology Process of (E)-10-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-12-oxo-7-((triethylsilyl)oxy)-2-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-4-en-6-yl acetate

There total 15 articles about (E)-10-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-12-oxo-7-((triethylsilyl)oxy)-2-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-4-en-6-yl acetate 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: 87.0%

: 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

: 108-24-7
acetic anhydride

: 1399680-03-5
(E)-10-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-12-oxo-7-((triethylsilyl)oxy)-2-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-4-en-6-yl acetate

Guidance literature:: With pyridine; at 23 ℃; for 24h; Inert atmosphere;
DOI:10.1021/ol301886g

Reference yield:

: 556-82-1
3-methyl-2-buten-1-ol

: 1399680-03-5
(E)-10-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-12-oxo-7-((triethylsilyl)oxy)-2-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-4-en-6-yl acetate

Guidance literature:: Multi-step reaction with 7 steps

1.1: dmap; triethylamine / dichloromethane / 0 - 23 °C

2.1: selenium(IV) oxide; salicylic acid; tert.-butylhydroperoxide / dichloromethane; benzene / 48 h / Inert atmosphere

3.1: n-butyllithium; potassium tert-butylate / hexane / 0.75 h / -78 - -50 °C / Inert atmosphere

3.2: 0.75 h / Inert atmosphere

4.1: dmap / toluene / 0 - 23 °C

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 23 °C / pH 7

6.1: 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

7.1: pyridine / 24 h / 23 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tert.-butylhydroperoxide; dmap; selenium(IV) oxide; n-butyllithium; potassium tert-butylate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; p-benzoquinone; salicylic acid; In hexane; dichloromethane; toluene; benzene; 2.1: |Riley Selenium Dioxide Oxidation;
DOI:10.1021/ol301886g

Reference yield:

: 141561-63-9
(((3-methylbut-2-en-1-yl)oxy)methanetrityl)tribenzene

: 1399680-03-5
(E)-10-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-12-oxo-7-((triethylsilyl)oxy)-2-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-4-en-6-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: selenium(IV) oxide; salicylic acid; tert.-butylhydroperoxide / dichloromethane; benzene / 48 h / Inert atmosphere

2.1: n-butyllithium; potassium tert-butylate / hexane / 0.75 h / -78 - -50 °C / Inert atmosphere

2.2: 0.75 h / Inert atmosphere

3.1: dmap / toluene / 0 - 23 °C

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 23 °C / pH 7

5.1: 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

6.1: pyridine / 24 h / 23 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tert.-butylhydroperoxide; dmap; selenium(IV) oxide; n-butyllithium; potassium tert-butylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; p-benzoquinone; salicylic acid; In hexane; dichloromethane; toluene; benzene; 1.1: |Riley Selenium Dioxide Oxidation;
DOI:10.1021/ol301886g