(E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

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Chemical Name:(E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene
CAS No.:223565-08-0
Molecular Formula:C₄₄H₆₆O₅Si
Molecular Weight:703.091
Hs Code.:

(E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

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Chemical Property of (E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

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Technology Process of (E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

There total 13 articles about (E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene 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%

: 57253-31-3
(E)-5-bromo-3-methylpentyl-2-ene

: 223565-02-4
(2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methanal

: (E)-(2R,4R,5R,7S,9S,10S,12R,1'R,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

: 223565-08-0
(E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

Guidance literature:: (E)-5-bromo-3-methylpentyl-2-ene; With magnesium; In diethyl ether;

(2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methanal; In diethyl ether; for 2h; Heating;
DOI:10.1039/b008159k

Reference yield:

: 130514-54-4
(1'S,3R,5S,6S)-(+)-6-<1'-(t-butyldiphenylsilyloxymethyl)propyl>-3,5-dimethyltetrahydropyran-2-one

: 223565-08-0
(E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

2.1: Amberlite resin IR 118

3.1: 90 mg / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

4.1: H₂; K₂CO₃ / Lindlar catalyst / pentane; ethyl acetate / 1 h / 20 °C

5.1: 40 mg / pyridinium toluene-p-sulfonate / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 36 percent / PhI(OAc)2; I₂ / cyclohexane / 7 h / 20 °C / Irradiation

7.1: 53 percent / K₂CO₃ / methanol / 1.5 h / 20 °C

8.1: 80 percent / N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 20 °C

9.1: Mg / diethyl ether

9.2: 70 percent / diethyl ether / 2 h / Heating

With dmap; n-butyllithium; tetrapropylammonium perruthennate; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; Amberlite resin IR 118; hydrogen; iodine; pyridinium p-toluenesulfonate; potassium carbonate; magnesium; 4-methylmorpholine N-oxide; triethylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; ethyl acetate; pentane; 9.2: Barbier reaction;
DOI:10.1039/b008159k

Reference yield:

: 223564-89-4
(2R,4R,5S/R,2'S/R,3'R,5'S,6'S,1''S)-8-{6-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-methoxy-3,5-dimethyltetrahydro-2H-pyran-2-yl}-2-ethyl-2,5-dihydroxy-4-methyloct-7-yn-1-yl acetate

: 223565-08-0
(E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: H₂; K₂CO₃ / Lindlar catalyst / pentane; ethyl acetate / 1 h / 20 °C

2.1: 40 mg / pyridinium toluene-p-sulfonate / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 36 percent / PhI(OAc)2; I₂ / cyclohexane / 7 h / 20 °C / Irradiation

4.1: 53 percent / K₂CO₃ / methanol / 1.5 h / 20 °C

5.1: 80 percent / N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 20 °C

6.1: Mg / diethyl ether

6.2: 70 percent / diethyl ether / 2 h / Heating

With tetrapropylammonium perruthennate; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; hydrogen; iodine; pyridinium p-toluenesulfonate; potassium carbonate; magnesium; 4-methylmorpholine N-oxide; Lindlar's catalyst; In methanol; diethyl ether; dichloromethane; cyclohexane; ethyl acetate; pentane; 6.2: Barbier reaction;
DOI:10.1039/b008159k