Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester
CAS No.:247200-09-5
Molecular Formula:C₅₅H₉₈O₁₁SSi₂
Molecular Weight:1023.61
Hs Code.:

Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester

Synonyms:Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester

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Chemical Property of Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester

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Technology Process of Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester

There total 7 articles about Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-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: 86.0%

: ((E)-(R)-6-Benzyloxy-1-methoxymethoxy-hex-2-enyl)-tributyl-stannane

: 247200-07-3
Toluene-4-sulfonic acid (1S,2R)-1-[(3R,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxo-heptyl]-2-methoxymethoxy-dodecyl ester

: 247200-09-5
Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester

Guidance literature:: With indium(III) chloride; In ethyl acetate; at -78 - 20 ℃;
DOI:10.1021/np990132+

Reference yield:

: 204572-66-7
(4R,5R)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octanal

: 247200-09-5
Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / InCl₃ / ethyl acetate / 3 h / -78 - 20 °C

2: 94 percent / pyridine / 12 h

3: 94 percent / H₂ / 5 percent Pd/C / ethyl acetate / 12 h

4: 89 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

5: 86 percent / InCl₃ / ethyl acetate / -78 - 20 °C

With indium(III) chloride; 4 A molecular sieve; hydrogen; pyridinium chlorochromate; palladium on activated charcoal; In pyridine; dichloromethane; ethyl acetate; 1: Substitution / 2: Tosylation / 3: Hydrogenation / 4: Oxidation / 5: Substitution;
DOI:10.1021/np990132+

Reference yield:

: 247200-04-0
(E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol

: 247200-09-5
Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-14-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-tetradec-10-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / pyridine / 12 h

2: 94 percent / H₂ / 5 percent Pd/C / ethyl acetate / 12 h

3: 89 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

4: 86 percent / InCl₃ / ethyl acetate / -78 - 20 °C

With indium(III) chloride; 4 A molecular sieve; hydrogen; pyridinium chlorochromate; palladium on activated charcoal; In pyridine; dichloromethane; ethyl acetate; 1: Tosylation / 2: Hydrogenation / 3: Oxidation / 4: Substitution;
DOI:10.1021/np990132+