C₆₇H₁₀₈O₈Si₃

Base Information

• Chemical Name: C₆₇H₁₀₈O₈Si₃
• CAS No.: 924656-61-1
• Molecular Formula: C₆₇H₁₀₈O₈Si₃
• Molecular Weight: 1125.85

Synonyms:C₆₇H₁₀₈O₈Si₃

Chemical Property of C₆₇H₁₀₈O₈Si₃

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of C₆₇H₁₀₈O₈Si₃

There total 63 articles about C₆₇H₁₀₈O₈Si₃ 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: 77.0%

C73H114O8SeSi3 (924656-75-7) → C67H108O8Si3 (924656-61-1)

Guidance literature:

With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1021/ja066772y

Reference yield:

(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-oxepan-3-ol (908866-07-9) → C67H108O8Si3 (924656-61-1)

Guidance literature:

Multi-step reaction with 46 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

1.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

2.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

3.1: 92 percent / PdCl₂; O₂; Cu(OAc)2 / H₂O; N,N-dimethyl-acetamide / 36 h / 20 °C

4.1: TBAF / tetrahydrofuran / 2.5 h / 20 °C

5.1: 178.3 mg / 4-methylmorpholine / CH₂Cl₂ / 20 °C

6.1: 57 percent / SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

7.1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

8.1: Et₃N / CH₂Cl₂ / 3 h / 20 °C

9.1: 254.8 mg / CSA / methanol; CH₂Cl₂ / 1 h / 0 °C

10.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

11.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

11.2: 265.9 mg / tetrahydrofuran / 0.5 h / 0 °C

12.1: 9-BBN / tetrahydrofuran / 20 °C

12.2: aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 3 h / 20 °C

13.1: H₂ / Pd(OH)2/C / methanol / 1 h / 20 °C

14.1: 263.7 mg / PPTS / CH₂Cl₂ / 1 h / 20 °C

15.1: t-BuOK / tetrahydrofuran / 0.33 h / 20 °C

15.2: n-Bu₄NI / tetrahydrofuran / 1 h / 20 °C

16.1: 171.6 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 - 0 °C

17.1: I₂; imidazole; PPh₃ / benzene / 0.5 h / 20 °C

18.1: 462.2 mg / t-BuOK / tetrahydrofuran / 0.75 h / 0 °C

19.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

19.2: aq. Cs₂CO₃ / tetrahydrofuran / 0.33 h / 20 °C

19.3: Pd(PPh₃)4 / tetrahydrofuran; dimethylformamide / 50 °C

20.1: BH₃*SMe₂ / tetrahydrofuran / 0 - 20 °C

20.2: 676.8 mg / aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 2.5 h / 20 °C

21.1: 98 percent / tetra-n-propylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h / 0 °C

22.1: Et₃N; LiHMDS / tetrahydrofuran / 1.17 h / -78 °C

23.1: 525.7 mg / aq. 4-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; tetrahydrofuran / 20 °C

24.1: 85 percent / DIBALH / tetrahydrofuran; hexane / 1.58 h / -78 °C

25.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

26.1: DDQ; phosphate buffer / CH₂Cl₂ / 0.75 h / 20 °C / pH 7

27.1: 478.1 mg / tetra-n-propylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

28.1: 51 percent / Zn(OTf)2 / CH₂Cl₂ / 20 °C

29.1: 86 percent / Et₃N / CH₂Cl₂ / 1.5 h / 0 - 20 °C

30.1: m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / -78 °C

30.2: 94 percent / CH₂Cl₂; hexane / -78 - 0 °C

31.1: 95 percent / LiDBB / tetrahydrofuran / 0.67 h / -78 °C

32.1: 99 percent / Et₃N / CH₂Cl₂ / 0.42 h / 0 °C

33.1: 79 percent / TBAF; AcOH / tetrahydrofuran / 11.5 h / 20 °C

34.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

35.1: K₂CO₃ / methanol / 20 °C

36.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / -78 °C

36.2: 54.6 mg / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -78 - 20 °C

37.1: 97 percent / HF*pyridine / tetrahydrofuran / 15.5 h / 20 °C

38.1: 89 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

39.1: CuCN / tetrahydrofuran / 0.33 h / 0 °C

39.2: tetrahydrofuran / -78 - 0 °C

40.1: 48.0 mg / N-iodosuccinimide / acetoni

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; methanol; N-iodo-succinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; phosphate buffer; samarium diiodide; tetrapropylammonium perruthennate; copper diacetate; copper(I) thiophene-2-carboxylate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; lithium 4,4′-di(tert-butyl)biphenyl; pyridine-SO₃ complex; triphenyl-arsane; dimethylsulfide borane complex; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; iodine; oxygen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; palladium dichloride; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 3.1: Wacker-Tsuji reaction / 11.2: Wittig reaction / 19.3: Suzuki-Miyaura coupling / 41.1: Stille coupling / 45.2: Wittig reaction;

DOI:10.1021/ja066772y

Reference yield:

(2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene → C67H108O8Si3 (924656-61-1)

Guidance literature:

Multi-step reaction with 47 steps

1.1: 9.10 g / CSA / methanol; CHCl₃ / 20 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

3.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

4.1: 92 percent / PdCl₂; O₂; Cu(OAc)2 / H₂O; N,N-dimethyl-acetamide / 36 h / 20 °C

5.1: TBAF / tetrahydrofuran / 2.5 h / 20 °C

6.1: 178.3 mg / 4-methylmorpholine / CH₂Cl₂ / 20 °C

7.1: 57 percent / SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

8.1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

9.1: Et₃N / CH₂Cl₂ / 3 h / 20 °C

10.1: 254.8 mg / CSA / methanol; CH₂Cl₂ / 1 h / 0 °C

11.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

12.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

12.2: 265.9 mg / tetrahydrofuran / 0.5 h / 0 °C

13.1: 9-BBN / tetrahydrofuran / 20 °C

13.2: aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 3 h / 20 °C

14.1: H₂ / Pd(OH)2/C / methanol / 1 h / 20 °C

15.1: 263.7 mg / PPTS / CH₂Cl₂ / 1 h / 20 °C

16.1: t-BuOK / tetrahydrofuran / 0.33 h / 20 °C

16.2: n-Bu₄NI / tetrahydrofuran / 1 h / 20 °C

17.1: 171.6 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 - 0 °C

18.1: I₂; imidazole; PPh₃ / benzene / 0.5 h / 20 °C

19.1: 462.2 mg / t-BuOK / tetrahydrofuran / 0.75 h / 0 °C

20.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

20.2: aq. Cs₂CO₃ / tetrahydrofuran / 0.33 h / 20 °C

20.3: Pd(PPh₃)4 / tetrahydrofuran; dimethylformamide / 50 °C

21.1: BH₃*SMe₂ / tetrahydrofuran / 0 - 20 °C

21.2: 676.8 mg / aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 2.5 h / 20 °C

22.1: 98 percent / tetra-n-propylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h / 0 °C

23.1: Et₃N; LiHMDS / tetrahydrofuran / 1.17 h / -78 °C

24.1: 525.7 mg / aq. 4-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; tetrahydrofuran / 20 °C

25.1: 85 percent / DIBALH / tetrahydrofuran; hexane / 1.58 h / -78 °C

26.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

27.1: DDQ; phosphate buffer / CH₂Cl₂ / 0.75 h / 20 °C / pH 7

28.1: 478.1 mg / tetra-n-propylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

29.1: 51 percent / Zn(OTf)2 / CH₂Cl₂ / 20 °C

30.1: 86 percent / Et₃N / CH₂Cl₂ / 1.5 h / 0 - 20 °C

31.1: m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / -78 °C

31.2: 94 percent / CH₂Cl₂; hexane / -78 - 0 °C

32.1: 95 percent / LiDBB / tetrahydrofuran / 0.67 h / -78 °C

33.1: 99 percent / Et₃N / CH₂Cl₂ / 0.42 h / 0 °C

34.1: 79 percent / TBAF; AcOH / tetrahydrofuran / 11.5 h / 20 °C

35.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

36.1: K₂CO₃ / methanol / 20 °C

37.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / -78 °C

37.2: 54.6 mg / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -78 - 20 °C

38.1: 97 percent / HF*pyridine / tetrahydrofuran / 15.5 h / 20 °C

39.1: 89 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

40.1: CuCN / tetrahydrofuran / 0.33 h / 0 °C

40.2: tetrahydrofuran / -78 - 0 °

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; methanol; N-iodo-succinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; phosphate buffer; samarium diiodide; tetrapropylammonium perruthennate; copper diacetate; copper(I) thiophene-2-carboxylate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; lithium 4,4′-di(tert-butyl)biphenyl; pyridine-SO₃ complex; triphenyl-arsane; dimethylsulfide borane complex; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; iodine; oxygen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; palladium dichloride; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 4.1: Wacker-Tsuji reaction / 12.2: Wittig reaction / 20.3: Suzuki-Miyaura coupling / 42.1: Stille coupling / 46.2: Wittig reaction;

DOI:10.1021/ja066772y

upstream raw materials:

C₇₃H₁₁₄O₈SeSi₃

((2R,4aR,6S,7R,9aS)-7-Benzyloxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-methanol

(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-oxepan-3-ol

(2S,3S)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexane-1,3-diol

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