(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

Base Information

Chemical Name:(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
CAS No.:477210-50-7
Molecular Formula:C₃₉H₅₀O₈S
Molecular Weight:678.887
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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: 76.0%

: 98-59-9
p-toluenesulfonyl chloride

: 477210-49-4
(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

: 477210-50-7
(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

Guidance literature:: With pyridine; at 0 ℃; for 4h;
DOI:10.1021/jo0259111

Reference yield:

: 149525-95-1
(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

: 477210-50-7
(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

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / Bu₄NF / tetrahydrofuran / 2 h / 20 °C

2: 76 percent / pyridine / 4 h / 0 °C

With pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/jo0259111

Reference yield:

: 113368-89-1
(-)-8-phenylmenthyl dimethyl phosphonoacetate

: 477210-50-7
(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

Guidance literature:: Multi-step reaction with 4 steps

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

2: NaBH₄

3: Bu₄NF

4: pyridine

With pyridine; sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; 1: Horner-Wadsworth-Emmons reaction / 2: Reduction / 3: desilylation / 4: tosylation;
DOI:10.1080/10426509908546209