ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzylloxy)ethyl]-9-(methanesulfonyl)-2-nonenoate

Base Information

Chemical Name:ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzylloxy)ethyl]-9-(methanesulfonyl)-2-nonenoate
CAS No.:544429-30-3
Molecular Formula:C₂₉H₄₀O₇S
Molecular Weight:532.698
Hs Code.:

Synonyms:ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzylloxy)ethyl]-9-(methanesulfonyl)-2-nonenoate

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Chemical Property of ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzylloxy)ethyl]-9-(methanesulfonyl)-2-nonenoate

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Technology Process of ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzylloxy)ethyl]-9-(methanesulfonyl)-2-nonenoate

There total 17 articles about ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzylloxy)ethyl]-9-(methanesulfonyl)-2-nonenoate 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: 96.0%

: 124-63-0
methanesulfonyl chloride

: 169898-02-6
ethyl (2E,5S,7R,8R)-9-hydroxy-8-methyl-7-benzyloxy-5-[2-(benzyloxy)ethyl]-2-nonenoate

: 544429-30-3
ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzylloxy)ethyl]-9-(methanesulfonyl)-2-nonenoate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1021/jo034011x

Reference yield:

: 10385-30-5
4-(benzyloxy)butanoic acid

: 544429-30-3
ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzylloxy)ethyl]-9-(methanesulfonyl)-2-nonenoate

Guidance literature:: Multi-step reaction with 16 steps

1.1: triethylamine / diethyl ether / 0 - 20 °C

2.1: 88 percent / n-butyllithium / diethyl ether; tetrahydrofuran; hexane / 1 h / -78 - 0 °C

3.1: NaHMDS / tetrahydrofuran / 0.5 h / -70 °C

3.2: 73 percent / tetrahydrofuran / 18 h / -50 °C

4.1: 76 percent / LiBH₄; methanol / tetrahydrofuran / 4 h / 20 °C

5.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

6.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

6.2: tetrahydrofuran / 2 h / -78 °C

7.1: 5.9 g / formic acid / diethyl ether; H₂O / 10 h / 20 °C

8.1: Bu₂BOTf; i-Pr₂EtN / CH₂Cl₂ / 1.08 h

8.2: CH₂Cl₂ / 3 h / -78 °C

8.3: 80 percent / H₂O₂ / CH₂Cl₂; methanol

9.1: 99 percent / LiBH₄; methanol / tetrahydrofuran

10.1: 97 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 0 °C

11.1: 79 percent / triflic acid / CH₂Cl₂; cyclohexane / 12 h / 0 °C

12.1: OsO₄; N-methylmorpholine-N-oxide / tetrahydrofuran; H₂O / 0 - 20 °C

13.1: 212 mg / NaIO₄ / tetrahydrofuran; H₂O / 8 h

14.1: 80 percent / LiCl; DBU / acetonitrile / 20 °C

15.1: 100 percent / aqueous HF / acetonitrile / 3 h / 20 °C

16.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.25 h / 0 °C

With methanol; dmap; sodium periodate; osmium(VIII) oxide; lithium borohydride; n-butyllithium; formic acid; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; sodium hexamethyldisilazane; Dess-Martin periodane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; water; acetonitrile; 6.1: Wittig olefination / 14.1: Horner-Emmons olefination;
DOI:10.1021/jo034011x

Reference yield:

: 100-39-0
benzyl bromide

: 544429-30-3
ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzylloxy)ethyl]-9-(methanesulfonyl)-2-nonenoate

Guidance literature:: Multi-step reaction with 17 steps

1.1: potassium hydroxide / toluene / 72 h / Heating

1.2: 97 percent / potassium hydroxide / H₂O / 24 h / Heating

2.1: triethylamine / diethyl ether / 0 - 20 °C

3.1: 88 percent / n-butyllithium / diethyl ether; tetrahydrofuran; hexane / 1 h / -78 - 0 °C

4.1: NaHMDS / tetrahydrofuran / 0.5 h / -70 °C

4.2: 73 percent / tetrahydrofuran / 18 h / -50 °C

5.1: 76 percent / LiBH₄; methanol / tetrahydrofuran / 4 h / 20 °C

6.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

7.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

7.2: tetrahydrofuran / 2 h / -78 °C

8.1: 5.9 g / formic acid / diethyl ether; H₂O / 10 h / 20 °C

9.1: Bu₂BOTf; i-Pr₂EtN / CH₂Cl₂ / 1.08 h

9.2: CH₂Cl₂ / 3 h / -78 °C

9.3: 80 percent / H₂O₂ / CH₂Cl₂; methanol

10.1: 99 percent / LiBH₄; methanol / tetrahydrofuran

11.1: 97 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 0 °C

12.1: 79 percent / triflic acid / CH₂Cl₂; cyclohexane / 12 h / 0 °C

13.1: OsO₄; N-methylmorpholine-N-oxide / tetrahydrofuran; H₂O / 0 - 20 °C

14.1: 212 mg / NaIO₄ / tetrahydrofuran; H₂O / 8 h

15.1: 80 percent / LiCl; DBU / acetonitrile / 20 °C

16.1: 100 percent / aqueous HF / acetonitrile / 3 h / 20 °C

17.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.25 h / 0 °C

With methanol; dmap; potassium hydroxide; sodium periodate; osmium(VIII) oxide; lithium borohydride; n-butyllithium; formic acid; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; sodium hexamethyldisilazane; Dess-Martin periodane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; water; toluene; acetonitrile; 7.1: Wittig olefination / 15.1: Horner-Emmons olefination;
DOI:10.1021/jo034011x