C₄₁H₆₀O₈Si

Base Information

• Chemical Name: C₄₁H₆₀O₈Si
• CAS No.: 147806-98-2
• Molecular Formula: C₄₁H₆₀O₈Si
• Molecular Weight: 709.008

Synonyms:C₄₁H₆₀O₈Si

Chemical Property of C₄₁H₆₀O₈Si

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of C₄₁H₆₀O₈Si

There total 33 articles about C₄₁H₆₀O₈Si 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:

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol (122821-81-2) → C41H60O8Si (147806-98-2)

Guidance literature:

Multi-step reaction with 33 steps

1: 94 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

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

3: 98 percent / 80percent TFA / toluene / 15 h / 0 °C

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

5: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

7: benzene / 2 h / 80 °C

8: 90 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

9: 98 percent / (+)-DET, Ti(OⁱPr)4, t-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -40 - -20 °C

10: 72 percent / SO₃*py, Et₃N / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

11: 87 percent / NaN(TMS)2 / tetrahydrofuran / 1 h / 0 °C

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.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

16: 98 percent / Swen oxidant

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

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

19: 92 percent / aq. LiOH / tetrahydrofuran / 1 h / 50 °C

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

21: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 0 deg C, 1 h, 2.) benzene, 80 deg C, 3 h

22: 82 percent / Lawesson's reagent / toluene / 3 h / 110 °C

23: 2.) I(CH₂)4I, pempidine / 1.) ether, from -78 to 10 deg C, 2.) ether, 1 h

24: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

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

26: 90 percent / CSA / methanol; CH₂Cl₂ / 1 h / 0 °C

27: 89 percent / PDC / dimethylformamide / 16 h / 25 °C

28: 82 percent / K₂CO₃ / methanol / 3 h / 25 °C

29: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 0 deg C, 1 h, 2.) benzene, 80 deg C, 5 h

30: 75 percent / Lawesson's reagent / toluene / 5 h / 110 °C

31: 2.) I(CH₂)4I, pempidine / 1.) ether, from -78 to 10 deg C, 2.) ether, 2 h

32: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

33: 90 percent / Swern oxidant

With Lawessons reagent; 1,2,2,6,6-pentamethylpiperidine; 2,6-dimethylpyridine; titanium(IV) isopropylate; 1,4-Diiodobutane; tert.-butylhydroperoxide; dmap; lithium hydroxide; sodium hydroxide; dipyridinium dichromate; borane-THF; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; Swern oxidant; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00046a063

Reference yield:

benzyl bromide (100-39-0) → C41H60O8Si (147806-98-2)

Guidance literature:

Multi-step reaction with 32 steps

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

2: 98 percent / 80percent TFA / toluene / 15 h / 0 °C

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

4: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

6: benzene / 2 h / 80 °C

7: 90 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

8: 98 percent / (+)-DET, Ti(OⁱPr)4, t-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -40 - -20 °C

9: 72 percent / SO₃*py, Et₃N / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

10: 87 percent / NaN(TMS)2 / tetrahydrofuran / 1 h / 0 °C

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.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

15: 98 percent / Swen oxidant

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

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

18: 92 percent / aq. LiOH / tetrahydrofuran / 1 h / 50 °C

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

20: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 0 deg C, 1 h, 2.) benzene, 80 deg C, 3 h

21: 82 percent / Lawesson's reagent / toluene / 3 h / 110 °C

22: 2.) I(CH₂)4I, pempidine / 1.) ether, from -78 to 10 deg C, 2.) ether, 1 h

23: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

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

25: 90 percent / CSA / methanol; CH₂Cl₂ / 1 h / 0 °C

26: 89 percent / PDC / dimethylformamide / 16 h / 25 °C

27: 82 percent / K₂CO₃ / methanol / 3 h / 25 °C

28: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 0 deg C, 1 h, 2.) benzene, 80 deg C, 5 h

29: 75 percent / Lawesson's reagent / toluene / 5 h / 110 °C

30: 2.) I(CH₂)4I, pempidine / 1.) ether, from -78 to 10 deg C, 2.) ether, 2 h

31: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

32: 90 percent / Swern oxidant

With Lawessons reagent; 1,2,2,6,6-pentamethylpiperidine; 2,6-dimethylpyridine; titanium(IV) isopropylate; 1,4-Diiodobutane; tert.-butylhydroperoxide; dmap; lithium hydroxide; sodium hydroxide; dipyridinium dichromate; borane-THF; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; Swern oxidant; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00046a063

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) → C41H60O8Si (147806-98-2)

Guidance literature:

Multi-step reaction with 32 steps

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

2: 98 percent / 80percent TFA / toluene / 15 h / 0 °C

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

4: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

6: benzene / 2 h / 80 °C

7: 90 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

8: 98 percent / (+)-DET, Ti(OⁱPr)4, t-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -40 - -20 °C

9: 72 percent / SO₃*py, Et₃N / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

10: 87 percent / NaN(TMS)2 / tetrahydrofuran / 1 h / 0 °C

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.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

15: 98 percent / Swen oxidant

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

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

18: 92 percent / aq. LiOH / tetrahydrofuran / 1 h / 50 °C

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

20: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 0 deg C, 1 h, 2.) benzene, 80 deg C, 3 h

21: 82 percent / Lawesson's reagent / toluene / 3 h / 110 °C

22: 2.) I(CH₂)4I, pempidine / 1.) ether, from -78 to 10 deg C, 2.) ether, 1 h

23: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

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

25: 90 percent / CSA / methanol; CH₂Cl₂ / 1 h / 0 °C

26: 89 percent / PDC / dimethylformamide / 16 h / 25 °C

27: 82 percent / K₂CO₃ / methanol / 3 h / 25 °C

28: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 0 deg C, 1 h, 2.) benzene, 80 deg C, 5 h

29: 75 percent / Lawesson's reagent / toluene / 5 h / 110 °C

30: 2.) I(CH₂)4I, pempidine / 1.) ether, from -78 to 10 deg C, 2.) ether, 2 h

31: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

32: 90 percent / Swern oxidant

With Lawessons reagent; 1,2,2,6,6-pentamethylpiperidine; 2,6-dimethylpyridine; titanium(IV) isopropylate; 1,4-Diiodobutane; tert.-butylhydroperoxide; dmap; lithium hydroxide; sodium hydroxide; dipyridinium dichromate; borane-THF; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; Swern oxidant; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00046a063

upstream raw materials:

benzyl bromide

((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

(2R,3S,4S,6S)-2-Allyl-6-benzyloxymethyl-tetrahydro-pyran-3,4-diol

Downstream raw materials:

oxepino<3,2-b>pyrano<2',3':5,6>pyrano<2,3-f>oxepin, 2-<(benzyloxy)methyl>-4-(benzyloxy)-10-hydroxy-9-<1-<(tert-butyldimethylsilyl)oxy>propanyl>hexadecahydro-5a,10-dimethyl-, <2R-<2α,4α,4aβ,5aβ,7aβ,9α,10β,12aα,13aα,14aα>>-

oxepino<3,2-b>pyrano<2',3':5,6>pyrano<2,3-f>oxepin, 2-<(benzyloxy)methyl>-4-(benzyloxy)-10-hydroxy-9-<1-<(tert-butyldimethylsilyl)oxy>propanyl>hexadecahydro-5a,10-dimethyl-, <2R-<2α,4α,4aβ,5aβ,7aβ,9α,10α,12aα,13aα,14aα>>-

Hemibrevetoxin-B

C₄₆H₇₈O₈SeSi₂

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