Toluene-4-sulfonic acid (E)-(1S,4R,5R)-10-benzyloxy-4-hydroxy-5-methoxymethoxy-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-dec-6-enyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (E)-(1S,4R,5R)-10-benzyloxy-4-hydroxy-5-methoxymethoxy-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-dec-6-enyl ester
CAS No.:220408-02-6
Molecular Formula:C₄₃H₆₈O₁₀S
Molecular Weight:777.073
Hs Code.:

Toluene-4-sulfonic acid (E)-(1S,4R,5R)-10-benzyloxy-4-hydroxy-5-methoxymethoxy-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-dec-6-enyl ester

Synonyms:Toluene-4-sulfonic acid (E)-(1S,4R,5R)-10-benzyloxy-4-hydroxy-5-methoxymethoxy-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-dec-6-enyl ester

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Chemical Property of Toluene-4-sulfonic acid (E)-(1S,4R,5R)-10-benzyloxy-4-hydroxy-5-methoxymethoxy-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-dec-6-enyl ester

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Technology Process of Toluene-4-sulfonic acid (E)-(1S,4R,5R)-10-benzyloxy-4-hydroxy-5-methoxymethoxy-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-dec-6-enyl ester

There total 9 articles about Toluene-4-sulfonic acid (E)-(1S,4R,5R)-10-benzyloxy-4-hydroxy-5-methoxymethoxy-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-dec-6-enyl 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%

: [(S)-4-Benzyloxy-1-((Z)-2-methoxymethoxy-vinyl)-butyl]-tributyl-stannane

: 220408-00-4
Toluene-4-sulfonic acid (S)-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-4-oxo-butyl ester

: 220408-02-6
Toluene-4-sulfonic acid (E)-(1S,4R,5R)-10-benzyloxy-4-hydroxy-5-methoxymethoxy-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-dec-6-enyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo982057y

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 220408-02-6
Toluene-4-sulfonic acid (E)-(1S,4R,5R)-10-benzyloxy-4-hydroxy-5-methoxymethoxy-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-dec-6-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / pyridine / 12 h / 20 °C

2: 90 percent / H₂ / Pd-C / ethyl acetate; ethanol / 12 h

3: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

4: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; boron trifluoride diethyl etherate; hydrogen; Dess-Martin periodane; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate; 1: Tosylation / 2: Catalytic hydrogenation / 3: Oxidation / 4: Addition;
DOI:10.1021/jo982057y

Reference yield:

: (4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octanal

: 220408-02-6
Toluene-4-sulfonic acid (E)-(1S,4R,5R)-10-benzyloxy-4-hydroxy-5-methoxymethoxy-1-[(2S,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-dec-6-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / InCl₃ / ethyl acetate / 3 h / -78 - 20 °C

2: pyridine / 12 h / 20 °C

3: 92 percent / TBAF / tetrahydrofuran / 12 h / 45 °C

4: 90 percent / pyridine / 12 h / 20 °C

5: 90 percent / H₂ / Pd-C / ethyl acetate; ethanol / 12 h

6: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

7: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; indium(III) chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; 1: Addition / 2: Tosylation / 3: Cyclization / 4: Tosylation / 5: Catalytic hydrogenation / 6: Oxidation / 7: Addition;
DOI:10.1021/jo982057y