C₄₆H₇₈O₈SeSi₂

Base Information

• Chemical Name: C₄₆H₇₈O₈SeSi₂
• CAS No.: 147806-79-9
• Molecular Formula: C₄₆H₇₈O₈SeSi₂
• Molecular Weight: 894.252

Synonyms:

Chemical Property of C₄₆H₇₈O₈SeSi₂

Chemical Property:

Purity/Quality:

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Technology Process of C₄₆H₇₈O₈SeSi₂

There total 49 articles about C₄₆H₇₈O₈SeSi₂ 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:

((3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol (132375-56-5) → C46H78O8SeSi2 (147806-79-9,147853-14-3)

Guidance literature:

Multi-step reaction with 43 steps

1: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

2: 98 percent / TFA / toluene / 0.25 h / 0 °C

3: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

4: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

6: benzene / 2 h / 80 °C

7: 85 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

8: 97 percent / (+)-diethyl tartrate ((+)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -20 °C

9: SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

10: 1.) NaN(SiMe₃)2 / 1.) THF, 1 h, 2.) THF, 0 deg C, 30 min

11: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

12: 90 percent / CSA / CH₂Cl₂ / 5 h / 0 °C

13: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

14: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF, 1 h

15: 98 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

16: 89 percent / benzene / 3 h / 25 °C

17: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 15 h

18: 92 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 50 °C

19: 95 percent / TBAF / tetrahydrofuran / 18 h / 25 °C

20: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, RT, 2 h, 2.) THF, toluene, reflux, 1 h

21: 82 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / toluene / 3 h / 110 °C

22: 1.) t-BuLi, 2.) (2-thienyl)cyanocopper lithium, 3.) 1,4-diiodobutane, pempidine

23: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 30 min

24: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 25 °C

25: 95 percent / CSA / CH₂Cl₂; methanol / 0.5 h / Ambient temperature

26: 94 percent / PDC / dimethylformamide / 16 h / 25 °C

27: 100 percent / K₂CO₃ / methanol / 3 h / 25 °C

28: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, RT, 2 h, 2.) THF, toluene, reflux, 1 h

29: 75 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / toluene / 5 h / 110 °C

30: 1.) t-BuLi, 2.) (2-thienyl)cyanocopper lithium, 3.) 1,4-diiodobutane, pempidine

31: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

32: 1.) oxalyl chloride, DMSO, 2.) DBU / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) toluene, 110 deg C, 2 h

33: 56 percent / diethyl ether / 4 h / -78 - -10 °C

34: 89 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4 h / 2068.6 Torr

35: 90 percent / 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1 h / Ambient temperature

36: 82 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 25 °C

37: 95 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

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

39: benzene / 3 h / 80 °C

40: 95 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h

41: 86 percent / CSA / CH₂Cl₂; methanol / 3 h / 0 °C

42: 90 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

43: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, HMPA, from -78 deg C to RT, 30 min

With Lawessons reagent; 1,2,2,6,6-pentamethylpiperidine; 2,6-dimethylpyridine; titanium(IV) isopropylate; 1,4-Diiodobutane; dmap; lithium hydroxide; sodium hydroxide; dipyridinium dichromate; n-butyllithium; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; thien-2-yl(cyano)copper lithium; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

Reference yield:

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol (122821-81-2) → C46H78O8SeSi2 (147806-79-9,147853-14-3)

Guidance literature:

Multi-step reaction with 44 steps

1: 80 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

2: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

3: 98 percent / TFA / toluene / 0.25 h / 0 °C

4: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

5: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

7: benzene / 2 h / 80 °C

8: 85 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

9: 97 percent / (+)-diethyl tartrate ((+)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -20 °C

10: SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

11: 1.) NaN(SiMe₃)2 / 1.) THF, 1 h, 2.) THF, 0 deg C, 30 min

12: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

13: 90 percent / CSA / CH₂Cl₂ / 5 h / 0 °C

14: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

15: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF, 1 h

16: 98 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

17: 89 percent / benzene / 3 h / 25 °C

18: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 15 h

19: 92 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 50 °C

20: 95 percent / TBAF / tetrahydrofuran / 18 h / 25 °C

21: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, RT, 2 h, 2.) THF, toluene, reflux, 1 h

22: 82 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / toluene / 3 h / 110 °C

23: 1.) t-BuLi, 2.) (2-thienyl)cyanocopper lithium, 3.) 1,4-diiodobutane, pempidine

24: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 30 min

25: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 25 °C

26: 95 percent / CSA / CH₂Cl₂; methanol / 0.5 h / Ambient temperature

27: 94 percent / PDC / dimethylformamide / 16 h / 25 °C

28: 100 percent / K₂CO₃ / methanol / 3 h / 25 °C

29: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, RT, 2 h, 2.) THF, toluene, reflux, 1 h

30: 75 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / toluene / 5 h / 110 °C

31: 1.) t-BuLi, 2.) (2-thienyl)cyanocopper lithium, 3.) 1,4-diiodobutane, pempidine

32: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

33: 1.) oxalyl chloride, DMSO, 2.) DBU / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) toluene, 110 deg C, 2 h

34: 56 percent / diethyl ether / 4 h / -78 - -10 °C

35: 89 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4 h / 2068.6 Torr

36: 90 percent / 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1 h / Ambient temperature

37: 82 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 25 °C

38: 95 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

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

40: benzene / 3 h / 80 °C

41: 95 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h

42: 86 percent / CSA / CH₂Cl₂; methanol / 3 h / 0 °C

43: 90 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

44: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, HMPA, from

With Lawessons reagent; 1,2,2,6,6-pentamethylpiperidine; 2,6-dimethylpyridine; titanium(IV) isopropylate; 1,4-Diiodobutane; dmap; lithium hydroxide; sodium hydroxide; dipyridinium dichromate; n-butyllithium; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; thien-2-yl(cyano)copper lithium; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

Reference yield:

(2R,3S,4S,6S)-2-Allyl-6-benzyloxymethyl-tetrahydro-pyran-3,4-diol (147806-43-7) → C46H78O8SeSi2 (147806-79-9,147853-14-3)

Guidance literature:

Multi-step reaction with 41 steps

1: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

2: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

4: benzene / 2 h / 80 °C

5: 85 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

6: 97 percent / (+)-diethyl tartrate ((+)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -20 °C

7: SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

8: 1.) NaN(SiMe₃)2 / 1.) THF, 1 h, 2.) THF, 0 deg C, 30 min

9: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

10: 90 percent / CSA / CH₂Cl₂ / 5 h / 0 °C

11: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

12: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF, 1 h

13: 98 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

14: 89 percent / benzene / 3 h / 25 °C

15: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 15 h

16: 92 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 50 °C

17: 95 percent / TBAF / tetrahydrofuran / 18 h / 25 °C

18: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, RT, 2 h, 2.) THF, toluene, reflux, 1 h

19: 82 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / toluene / 3 h / 110 °C

20: 1.) t-BuLi, 2.) (2-thienyl)cyanocopper lithium, 3.) 1,4-diiodobutane, pempidine

21: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 30 min

22: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 25 °C

23: 95 percent / CSA / CH₂Cl₂; methanol / 0.5 h / Ambient temperature

24: 94 percent / PDC / dimethylformamide / 16 h / 25 °C

25: 100 percent / K₂CO₃ / methanol / 3 h / 25 °C

26: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, RT, 2 h, 2.) THF, toluene, reflux, 1 h

27: 75 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / toluene / 5 h / 110 °C

28: 1.) t-BuLi, 2.) (2-thienyl)cyanocopper lithium, 3.) 1,4-diiodobutane, pempidine

29: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

30: 1.) oxalyl chloride, DMSO, 2.) DBU / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) toluene, 110 deg C, 2 h

31: 56 percent / diethyl ether / 4 h / -78 - -10 °C

32: 89 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4 h / 2068.6 Torr

33: 90 percent / 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1 h / Ambient temperature

34: 82 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 25 °C

35: 95 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

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

37: benzene / 3 h / 80 °C

38: 95 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h

39: 86 percent / CSA / CH₂Cl₂; methanol / 3 h / 0 °C

40: 90 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

41: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, HMPA, from -78 deg C to RT, 30 min

With Lawessons reagent; 1,2,2,6,6-pentamethylpiperidine; 2,6-dimethylpyridine; titanium(IV) isopropylate; 1,4-Diiodobutane; dmap; lithium hydroxide; sodium hydroxide; dipyridinium dichromate; n-butyllithium; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; thien-2-yl(cyano)copper lithium; triethylamine; triphenylphosphine; cesium fluoride; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

upstream raw materials:

oxepino<3,2-b>pyrano<2',3':5,6>pyrano<2,3-f>oxepin-2-propanoate, 4,10-bis<(tert-butyldimethylsilyl)oxy>-9-(2-formylethyl)hexadecahydro-5a,10-dimethyl-, <2R-<2α,4α,4aβ,5aβ,7aβ,9α,10β,12aα,13aα,14aα>>-, methyl ester

Triphenyl-(3-phenylselanyl-propyl)-phosphonium; iodide

((3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

Downstream raw materials:

Hemibrevetoxin-B

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