(Z)-(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-4,6-dimethyl-7-oxo-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Base Information

Chemical Name:(Z)-(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-4,6-dimethyl-7-oxo-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
CAS No.:217026-01-2
Molecular Formula:C₃₁H₅₀O₄Si
Molecular Weight:514.821
Hs Code.:

Synonyms:(Z)-(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-4,6-dimethyl-7-oxo-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

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Chemical Property of (Z)-(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-4,6-dimethyl-7-oxo-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

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Technology Process of (Z)-(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-4,6-dimethyl-7-oxo-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

There total 5 articles about (Z)-(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-4,6-dimethyl-7-oxo-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester 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%

: meso-(2R,3r,4S)-3-((tert-butyldimethylsilyl)oxy)-2,4-dimethylpentanedial

: 155795-46-3
[bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

: 217026-01-2
(Z)-(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-4,6-dimethyl-7-oxo-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Guidance literature:: With 18-crown-6 ether; potassium hexamethylsilazane; at -85 ℃; for 6.25h;
DOI:10.1080/10426509908546208

Reference yield: 25.0%

: meso-(2R,3r,4S)-3-((tert-butyldimethylsilyl)oxy)-2,4-dimethylpentanedial

: 155795-46-3
[bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

: (2E,7E)-(4S,5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethyl-nona-2,7-dienedioic acid bis-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

: 217026-01-2
(Z)-(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-4,6-dimethyl-7-oxo-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

: (2Z,7Z)-(4S,5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethyl-nona-2,7-dienedioic acid bis-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

: (2Z,7E)-(4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethyl-nona-2,7-dienedioic acid bis-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

Guidance literature:: [bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

meso-(2R,3r,4S)-3-((tert-butyldimethylsilyl)oxy)-2,4-dimethylpentanedial; In tetrahydrofuran; toluene; at 0 ℃; for 2h;
DOI:10.1021/jo981102z

Reference yield:

: 65253-04-5
(-)-8-phenylmenthol

: 217026-01-2
(Z)-(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-4,6-dimethyl-7-oxo-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 89 percent / DMAP / toluene / Heating

2.1: 18-crown-6; potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.2: tetrahydrofuran; toluene / -90 °C

With dmap; 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; 1.1: Esterification / 2.1: Metallation / 2.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo981102z