(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene

Base Information

Chemical Name:(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene
CAS No.:132375-83-8
Molecular Formula:C₄₈H₇₂O₆S₂Si₂
Molecular Weight:865.399
Hs Code.:

(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene

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Chemical Property of (2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene

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Technology Process of (2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene

There total 33 articles about (2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene 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:

: 132375-82-7
(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-octahydro-1,8,10-trioxa-anthracen-3-one

: 75-08-1
ethanethiol

: 132375-83-8
(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene

Guidance literature:: With zinc trifluoromethanesulfonate; In dichloromethane; at 25 ℃; for 5h;

Reference yield:

: 100-39-0
benzyl bromide

: 132375-83-8
(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene

Guidance literature:: Multi-step reaction with 25 steps

1: 1) n-Bu₂SnO, 2) CsF / 1) MeOH, 65 deg C, 1 h, 2) DMF, 25 deg C, 18 h

2: 96 percent / imidazole / dimethylformamide / 12 h / 25 °C

3: 1) ozone, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C

4: benzene / 12 h / 25 °C

5: 96 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

6: 92 percent / (+)-DET, Ti(IOPr)4, t-BuOOH, 4 Angstroem molecular sieve / CH₂Cl₂ / 48 h / -20 °C

7: SO₃*Py, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

8: NaN(TMS)2 / tetrahydrofuran / 1 h / 0 °C

9: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / -20 - 0 °C

10: 80 percent / camphersulfonic acid / CH₂Cl₂ / 2 h / 0 °C

11: 99 percent / imidazole / dimethylformamide / 12 h / 25 °C

12: 1) 9-BBN, 2) NaOH, H₂O₂ / 1) THF, 0 deg C, 2 h, 2) 0 deg C, 1 h

13: oxalyl chloride, DMSO, NEt₃ / CH₂Cl₂ / 1 h / -78 °C

14: benzene / 12 h / 25 °C

15: 96 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

16: 92 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieve / CH₂Cl₂ / 12 h / -20 °C

17: SO₃*py, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

18: benzene / 12 h / 25 °C

19: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C

20: 80 percent / camphersulfonic acid / CH₂Cl₂ / 0 - 25 °C

21: 1) ozone, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C, 2) 25 deg C, 3 h

22: NaBH₄ / methanol / 0 °C

23: 93 percent / imidazole / dimethylformamide / 1 h / 0 °C

24: 93 percent / oxalyl chloride, DMSO, NEt₃ / CH₂Cl₂ / 1 h / -78 °C

25: Zn(OTf)2 / CH₂Cl₂ / 5 h / 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

Reference yield:

: 132375-57-6
(3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

: 132375-83-8
(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene

Guidance literature:: Multi-step reaction with 30 steps

1: CH₂Cl₂ / 18 h / 25 °C

2: 1) L-selectride, t-BuOH, 2) NaOH, H₂O₂ / 1) THF, -78 deg C, 1 h, 2) 0 deg C, 1 h

3: DIBAH / CH₂Cl₂ / 1 h / -78 °C

4: 95 percent / imidazole / dimethylformamide / 2 h / 0 - 25 °C

5: 90 percent / camphersulfonic acid / methanol / 4 h / 25 °C

6: 1) n-Bu₂SnO, 2) CsF / 1) MeOH, 65 deg C, 1 h, 2) DMF, 25 deg C, 18 h

7: 96 percent / imidazole / dimethylformamide / 12 h / 25 °C

8: 1) ozone, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C

9: benzene / 12 h / 25 °C

10: 96 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

11: 92 percent / (+)-DET, Ti(IOPr)4, t-BuOOH, 4 Angstroem molecular sieve / CH₂Cl₂ / 48 h / -20 °C

12: SO₃*Py, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

13: NaN(TMS)2 / tetrahydrofuran / 1 h / 0 °C

14: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / -20 - 0 °C

15: 80 percent / camphersulfonic acid / CH₂Cl₂ / 2 h / 0 °C

16: 99 percent / imidazole / dimethylformamide / 12 h / 25 °C

17: 1) 9-BBN, 2) NaOH, H₂O₂ / 1) THF, 0 deg C, 2 h, 2) 0 deg C, 1 h

18: oxalyl chloride, DMSO, NEt₃ / CH₂Cl₂ / 1 h / -78 °C

19: benzene / 12 h / 25 °C

20: 96 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

21: 92 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieve / CH₂Cl₂ / 12 h / -20 °C

22: SO₃*py, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

23: benzene / 12 h / 25 °C

24: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C

25: 80 percent / camphersulfonic acid / CH₂Cl₂ / 0 - 25 °C

26: 1) ozone, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C, 2) 25 deg C, 3 h

27: NaBH₄ / methanol / 0 °C

28: 93 percent / imidazole / dimethylformamide / 1 h / 0 °C

29: 93 percent / oxalyl chloride, DMSO, NEt₃ / CH₂Cl₂ / 1 h / -78 °C

30: Zn(OTf)2 / CH₂Cl₂ / 5 h / 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; L-Selectride; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; cesium fluoride; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;