(S)-2-hydroxy-2-[(2S,5R)-5-((R)-1-hydroxytridecyl)tetrahydrofuran-2-yl]-ethyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (S)-2-hydroxy-2-[(2S,5R)-5-((R)-1-hydroxytridecyl)tetrahydrofuran-2-yl]-ethyl 4-methylbenzenesulfonate
• CAS No.: 699010-02-1
• Molecular Formula: C₂₆H₄₄O₆S
• Molecular Weight: 484.698
• Mol file: 699010-02-1.mol

Synonyms:(S)-2-hydroxy-2-[(2S,5R)-5-((R)-1-hydroxytridecyl)tetrahydrofuran-2-yl]-ethyl 4-methylbenzenesulfonate

Chemical Property of (S)-2-hydroxy-2-[(2S,5R)-5-((R)-1-hydroxytridecyl)tetrahydrofuran-2-yl]-ethyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-hydroxy-2-[(2S,5R)-5-((R)-1-hydroxytridecyl)tetrahydrofuran-2-yl]-ethyl 4-methylbenzenesulfonate

There total 8 articles about (S)-2-hydroxy-2-[(2S,5R)-5-((R)-1-hydroxytridecyl)tetrahydrofuran-2-yl]-ethyl 4-methylbenzenesulfonate 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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + (1S)-1-{(2S,5R)-5-[(1R)-1-hydroxytridecyl]tetrahydrofuran-2-yl}ethane-1,2-diol (699010-01-0) → (S)-2-hydroxy-2-[(2S,5R)-5-((R)-1-hydroxytridecyl)tetrahydrofuran-2-yl]-ethyl 4-methylbenzenesulfonate (699010-02-1)

Guidance literature:

(1S)-1-{(2S,5R)-5-[(1R)-1-hydroxytridecyl]tetrahydrofuran-2-yl}ethane-1,2-diol; With di(n-butyl)tin oxide; In benzene; for 3h; Reflux; Inert atmosphere;

p-toluenesulfonyl chloride; In benzene; at 20 ℃; for 0.166667h; Inert atmosphere;

With tetrabutylammomium bromide; In benzene; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo9012578

Reference yield:

trans ethyl heptadec-4-enoate (145285-55-8) → (S)-2-hydroxy-2-[(2S,5R)-5-((R)-1-hydroxytridecyl)tetrahydrofuran-2-yl]-ethyl 4-methylbenzenesulfonate (699010-02-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 88 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -78 °C

2.1: DIBAL-H / CH₂Cl₂; hexane / 2 h / -60 °C

2.2: 96 percent / sodium hydride / CH₂Cl₂; hexane; tetrahydrofuran / 1.5 h / -40 - 20 °C

3.1: 98 percent / NaOH; NaHCO₃ / methanol; H₂O / 5 h / Heating

4.1: oxalyl chloride; DMF / CH₂Cl₂ / 2 h / cooling

5.1: 3.03 g / sodium hydride / CH₂Cl₂ / 1 h / 0 °C

6.1: acetic acid; KMnO₄; adogen 464 / acetone / 1 h / -30 - -10 °C

7.1: 90 percent / NaBH₄ / H₂O; tetrahydrofuran / 2 h / -10 - 0 °C

8.1: Bu₂SnO / benzene / 3 h / Heating

8.2: 98 percent / tetrabutylammonium bromide / benzene / 0.5 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; potassium permanganate; oxalyl dichloride; adogen 464; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; acetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; benzene;

DOI:10.1021/jo049909g

Reference yield:

(4E)-heptadec-4-enal (184435-63-0) → (S)-2-hydroxy-2-[(2S,5R)-5-((R)-1-hydroxytridecyl)tetrahydrofuran-2-yl]-ethyl 4-methylbenzenesulfonate (699010-02-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: DIBAL-H / CH₂Cl₂; hexane / 2 h / -60 °C

1.2: 96 percent / sodium hydride / CH₂Cl₂; hexane; tetrahydrofuran / 1.5 h / -40 - 20 °C

2.1: 98 percent / NaOH; NaHCO₃ / methanol; H₂O / 5 h / Heating

3.1: oxalyl chloride; DMF / CH₂Cl₂ / 2 h / cooling

4.1: 3.03 g / sodium hydride / CH₂Cl₂ / 1 h / 0 °C

5.1: acetic acid; KMnO₄; adogen 464 / acetone / 1 h / -30 - -10 °C

6.1: 90 percent / NaBH₄ / H₂O; tetrahydrofuran / 2 h / -10 - 0 °C

7.1: Bu₂SnO / benzene / 3 h / Heating

7.2: 98 percent / tetrabutylammonium bromide / benzene / 0.5 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; potassium permanganate; oxalyl dichloride; adogen 464; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; acetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; benzene;

DOI:10.1021/jo049909g

upstream raw materials:

p-toluenesulfonyl chloride

(1S)-1-{(2S,5R)-5-[(1R)-1-hydroxytridecyl]tetrahydrofuran-2-yl}ethane-1,2-diol

trans ethyl heptadec-4-enoate

(4E)-heptadec-4-enal