(E)-(4R,6R,8S)-6-benzyloxy-4,8,9-trihydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Base Information

• Chemical Name: (E)-(4R,6R,8S)-6-benzyloxy-4,8,9-trihydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• CAS No.: 477210-49-4
• Molecular Formula: C₃₂H₄₄O₆
• Molecular Weight: 524.698
• Mol file: 477210-49-4.mol

Synonyms:(E)-(4R,6R,8S)-6-benzyloxy-4,8,9-trihydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Chemical Property of (E)-(4R,6R,8S)-6-benzyloxy-4,8,9-trihydroxynon-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 (E)-(4R,6R,8S)-6-benzyloxy-4,8,9-trihydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

There total 4 articles about (E)-(4R,6R,8S)-6-benzyloxy-4,8,9-trihydroxynon-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: 80.0%

(E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (149525-95-1) → (E)-(4R,6R,8S)-6-benzyloxy-4,8,9-trihydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (477210-49-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jo0259111

Reference yield:

(-)-8-phenylmenthyl dimethyl phosphonoacetate (113368-89-1) → (E)-(4R,6R,8S)-6-benzyloxy-4,8,9-trihydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (477210-49-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / KHMDS; 18-C-6 / tetrahydrofuran / -78 °C

2: NaBH₄

3: Bu₄NF

With sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; 1: Horner-Wadsworth-Emmons reaction / 2: Reduction / 3: desilylation;

DOI:10.1080/10426509908546209

Reference yield:

meso-(2R,4s,6S)-4-(benzyloxy)-2,6-bis((tert-butyldiphenylsilyl)oxy)heptanedial → (E)-(4R,6R,8S)-6-benzyloxy-4,8,9-trihydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (477210-49-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / KHMDS; 18-C-6 / tetrahydrofuran / -78 °C

2: NaBH₄

3: Bu₄NF

With sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; 1: Horner-Wadsworth-Emmons reaction / 2: Reduction / 3: desilylation;

DOI:10.1080/10426509908546209

upstream raw materials:

(E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

(-)-8-phenylmenthyl dimethyl phosphonoacetate

(E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Downstream raw materials:

(E)-(4R,6R)-6-Benzyloxy-4-hydroxy-7-(S)-oxiranyl-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(E)-(4R,6R,8S)-6-benzyloxy-4,8-dihydroxy-9-(toluene-4-sulfonyloxy)non-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester