Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester

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Chemical Name:Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester
CAS No.:199792-34-2
Molecular Formula:C₄₈H₆₆O₉SSi₂
Molecular Weight:875.284
Hs Code.:

Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester

Synonyms:Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester

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Chemical Property of Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester

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Technology Process of Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester

There total 36 articles about Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-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: 90.0%

: 98-59-9
p-toluenesulfonyl chloride

: 199792-05-7
(2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-hydroxy-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol

: 199792-34-2
Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 20h; Ambient temperature;
DOI:10.1016/S0040-4039(97)10107-1

Reference yield:

: (Z)-5-{(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-4-(tert-butyl-dimethyl-silanyloxy)-pent-2-enoic acid methyl ester

: 199792-34-2
Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 22 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / Ambient temperature

2: 1) NaH, 2) t-BuOK / 1) THF, room temperature, 2 h, 2) MeOH, room temperature, 18 h

3: 75 percent / TfOH / diethyl ether / 0.17 h / Ambient temperature

4: 100 percent / LiAlH₄ / diethyl ether / 0.5 h / -5 °C

5: 95 percent / NEt₃, DMAP / CH₂Cl₂ / 9 h / Ambient temperature

6: 100 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / Ambient temperature

7: 44 percent / H₂ / Pd(OH)2-C / ethanol; ethyl acetate / 168 h / 760 Torr / Ambient temperature

8: 96 percent / p-TsOH*H₂O / 0.5 h / Ambient temperature

9: 99 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 31 h / Ambient temperature

10: 94 percent / p-TsOH*H₂O / methanol / 0.83 h / Ambient temperature

11: 83 percent / NEt₃, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; potassium tert-butylate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate;
DOI:10.1016/S0040-4020(97)10254-X

Reference yield:

: 199792-25-1
{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-acetic acid methyl ester

: 199792-34-2
Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / LiAlH₄ / diethyl ether / 0.5 h / -5 °C

2: 95 percent / NEt₃, DMAP / CH₂Cl₂ / 9 h / Ambient temperature

3: 100 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / Ambient temperature

4: 44 percent / H₂ / Pd(OH)2-C / ethanol; ethyl acetate / 168 h / 760 Torr / Ambient temperature

5: 96 percent / p-TsOH*H₂O / 0.5 h / Ambient temperature

6: 99 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 31 h / Ambient temperature

7: 94 percent / p-TsOH*H₂O / methanol / 0.83 h / Ambient temperature

8: 83 percent / NEt₃, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate;
DOI:10.1016/S0040-4020(97)10254-X