5-Undecanone, 1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-hydroxy-4,4,6,8-tetrameth yl-11-[(1R,2R)-2-[(phenylmethoxy)methyl]cyclopropyl]-, (3S,6R,7S,8S)-

Base Information

Chemical Name:5-Undecanone, 1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-hydroxy-4,4,6,8-tetrameth yl-11-[(1R,2R)-2-[(phenylmethoxy)methyl]cyclopropyl]-, (3S,6R,7S,8S)-
CAS No.:371785-05-6
Molecular Formula:C38H70O5Si2
Molecular Weight:663.142
Hs Code.:
Mol file:371785-05-6.mol

5-Undecanone,
1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-hydroxy-4,4,6,8-tetrameth
yl-11-[(1R,2R)-2-[(phenylmethoxy)methyl]cyclopropyl]-, (3S,6R,7S,8S)-

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Chemical Property of 5-Undecanone, 1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-hydroxy-4,4,6,8-tetrameth yl-11-[(1R,2R)-2-[(phenylmethoxy)methyl]cyclopropyl]-, (3S,6R,7S,8S)-

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Technology Process of 5-Undecanone, 1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-hydroxy-4,4,6,8-tetrameth yl-11-[(1R,2R)-2-[(phenylmethoxy)methyl]cyclopropyl]-, (3S,6R,7S,8S)-

There total 13 articles about 5-Undecanone, 1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-hydroxy-4,4,6,8-tetrameth yl-11-[(1R,2R)-2-[(phenylmethoxy)methyl]cyclopropyl]-, (3S,6R,7S,8S)- 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:

: 187527-25-9
(-)-(5S)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethylheptan-3-one

: 371784-85-9
(S)-5-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-2-methyl-pentan-1-ol

: 371785-05-6
(3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8-tetramethyl-undecan-5-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.0666667h;

Reference yield:

: 371784-87-1
(Z)-(S)-5-Benzyloxy-2-methyl-pent-3-en-1-ol

: 371785-05-6
(3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8-tetramethyl-undecan-5-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: 89 percent / imidazole / dimethylformamide / 1 h / 25 °C

2.1: 75 percent / H₂ / Pd/C / methanol; tetrahydrofuran / 10 h / 50 °C / 760.05 Torr

3.1: 93 percent / PPh₃; imidazole; I₂ / 4-DMAP / acetonitrile; diethyl ether / 1 h / 25 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 72 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 2.5 h / -78 - -30 °C

5.1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 25 °C

6.1: 95 percent / NaBH₄; NiCl₂; H₂ / ethylene diamine / ethanol / 1 h / 0 °C / 760.05 Torr

7.1: 99 percent / Et₂Zn; DME; cyclo-(S,S)-(n-Bu)B-[OCH(CONMe₂)]2 / CH₂Cl₂ / 6 h / 20 °C

8.1: Ag₂O; TBAI / toluene / 24 h / 25 - 50 °C

9.1: 499 mg / TBAF / tetrahydrofuran / 4 h / 25 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 25 °C

11.1: LDA / tetrahydrofuran / -78 - -40 °C

11.2: 1.14 g / tetrahydrofuran / 0.07 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; 1,2-dimethoxyethane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; iodine; diethylzinc; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; triphenylphosphine; nickel dichloride; silver(l) oxide; (4S,5S)-2-butyl-N⁴,N⁴,N⁵,N⁵-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide; lithium diisopropyl amide; dmap; palladium on activated charcoal; ethylenediamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7.1: Charette cyclopropanation;
DOI:10.1021/ja011338b

Reference yield:

: 371784-89-3
(S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-pentanol

: 371785-05-6
(3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8-tetramethyl-undecan-5-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / PPh₃; imidazole; I₂ / 4-DMAP / acetonitrile; diethyl ether / 1 h / 25 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 72 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 2.5 h / -78 - -30 °C

3.1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 25 °C

4.1: 95 percent / NaBH₄; NiCl₂; H₂ / ethylene diamine / ethanol / 1 h / 0 °C / 760.05 Torr

5.1: 99 percent / Et₂Zn; DME; cyclo-(S,S)-(n-Bu)B-[OCH(CONMe₂)]2 / CH₂Cl₂ / 6 h / 20 °C

6.1: Ag₂O; TBAI / toluene / 24 h / 25 - 50 °C

7.1: 499 mg / TBAF / tetrahydrofuran / 4 h / 25 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 25 °C

9.1: LDA / tetrahydrofuran / -78 - -40 °C

9.2: 1.14 g / tetrahydrofuran / 0.07 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; 1,2-dimethoxyethane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; iodine; diethylzinc; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; triphenylphosphine; nickel dichloride; silver(l) oxide; (4S,5S)-2-butyl-N⁴,N⁴,N⁵,N⁵-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide; lithium diisopropyl amide; dmap; ethylenediamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 5.1: Charette cyclopropanation;
DOI:10.1021/ja011338b