(Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Base Information

• Chemical Name: (Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• CAS No.: 477210-37-0
• Molecular Formula: C₅₆H₇₀O₅Si₂
• Molecular Weight: 879.34
• Mol file: 477210-37-0.mol

Synonyms:(Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Chemical Property of (Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

There total 3 articles about (Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-oxoocta-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: 88.0%

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial (134341-56-3) + [bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (155795-46-3) → (Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (477210-37-0)

Guidance literature:

[bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial; In tetrahydrofuran; toluene; at -78 ℃; Further stages.;

DOI:10.1021/jo0259111

Reference yield:

meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol (134522-14-8) → (Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (477210-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / H₅IO₆ / tetrahydrofuran / 0 - 20 °C

2.1: NaHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.2: 88 percent / tetrahydrofuran; toluene / -78 °C

With sodium hexamethyldisilazane; periodic acid; In tetrahydrofuran; toluene; 2.1: asymmetric Horner-Wadsworth-Emmons reaction / 2.2: asymmetric Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo0259111

Reference yield:

3,6-bis(tert-butyldiphenylsilyloxy)cyclohex-1-ene → (Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (477210-37-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 73 percent / RuCl₃ hydrate; NaIO₄ / ethyl acetate; acetonitrile; H₂O / 0.02 h / 0 °C

2.1: 96 percent / H₅IO₆ / tetrahydrofuran / 0 - 20 °C

3.1: NaHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.2: 88 percent / tetrahydrofuran; toluene / -78 °C

With ruthenium trichloride; sodium periodate; sodium hexamethyldisilazane; periodic acid; In tetrahydrofuran; water; ethyl acetate; toluene; acetonitrile; 3.1: asymmetric Horner-Wadsworth-Emmons reaction / 3.2: asymmetric Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo0259111

upstream raw materials:

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial

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

meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol

Downstream raw materials:

(Z)-(4S,7R)-4,8-bis(tert-butyldiphenylsilyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester