(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

Base Information

• Chemical Name: (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
• CAS No.: 477210-42-7
• Molecular Formula: C₅₆H₇₂O₅Si₂
• Molecular Weight: 881.356
• Mol file: 477210-42-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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: 59.0%

(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) → (Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester + (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 (477210-42-7)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃;

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)-4,8-bis(tert-butyldiphenylsilyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (477210-42-7)

Guidance literature:

Multi-step reaction with 3 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

3.1: 59 percent / NaBH₄ / tetrahydrofuran; methanol / 0 °C

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

DOI:10.1021/jo0259111

Reference yield:

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial (134341-56-3) → (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 (477210-42-7)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 88 percent / tetrahydrofuran; toluene / -78 °C

2.1: 59 percent / NaBH₄ / tetrahydrofuran; methanol / 0 °C

With sodium tetrahydroborate; sodium hexamethyldisilazane; In tetrahydrofuran; methanol; toluene; 1.1: asymmetric Horner-Wadsworth-Emmons reaction / 1.2: asymmetric Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo0259111

upstream raw materials:

(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

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

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