Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester
CAS No.:165961-06-8
Molecular Formula:C₄₀H₇₂O₁₀SSi
Molecular Weight:773.157
Hs Code.:

Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

There total 15 articles about Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl 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: 42.0%

: 98-59-9
p-toluenesulfonyl chloride

: 165961-05-7
(+)-(4R,15R,16R,19R,20R,23R,24S)-1-O-(tert-Butyldimethylsilyl)-16,19:20,23-diepoxy-4-O-(methoxymethyl)-1,4,15,24,25-pentahydroxypentacosane

: 165961-06-8
Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

Guidance literature:: With pyridine; at -20 ℃; for 48h;
DOI:10.1021/jo00119a019

Reference yield:

: 165961-00-2
(R)-13-(tert-Butyl-dimethyl-silanyloxy)-10-methoxymethoxy-tridecan-1-ol

: 165961-06-8
Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / pyridine / 41 h / -20 °C

2: 92 percent / NaH / tetrahydrofuran / 1.) 30 min, 2.) room temp., 2 h

3: 95 percent / aq. magnesium monoperoxyphthalate / ethanol / 12 h / Ambient temperature

4: 83 percent / n-BuLi / hexane; 1,2-dimethoxy-ethane / 0.17 h / Ambient temperature

5: 60 percent / sodium amalgam / ethanol / 24 h / Ambient temperature

6: 42 percent / pyridine / 48 h / -20 °C

With pyridine; sodium amalgam; n-butyllithium; sodium hydride; magnesium monoperoxyphthalate hexahydrate; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane;
DOI:10.1021/jo00119a019

Reference yield:

: 165960-93-0
(-)-(2R,3R,6R,7R,10R,11S)-11,12-Dihydroxy-1,2:3,6:7,10-triepoxydodecane

: 165961-06-8
Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / n-BuLi / hexane; 1,2-dimethoxy-ethane / 0.17 h / Ambient temperature

2: 60 percent / sodium amalgam / ethanol / 24 h / Ambient temperature

3: 42 percent / pyridine / 48 h / -20 °C

With pyridine; sodium amalgam; n-butyllithium; In 1,2-dimethoxyethane; ethanol; hexane;
DOI:10.1021/jo00119a019