C₅₁H₈₄O₉Si₃

Base Information

Chemical Name:C₅₁H₈₄O₉Si₃
CAS No.:221381-14-2
Molecular Formula:C₅₁H₈₄O₉Si₃
Molecular Weight:925.479
Hs Code.:

C<sub>51</sub>H<sub>84</sub>O<sub>9</sub>Si<sub>3</sub>

Synonyms:C₅₁H₈₄O₉Si₃

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Chemical Property of C₅₁H₈₄O₉Si₃

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Technology Process of C₅₁H₈₄O₉Si₃

There total 45 articles about C₅₁H₈₄O₉Si₃ 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:

: 122821-82-3
2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

: 221381-14-2
C₅₁H₈₄O₉Si₃

Guidance literature:: Multi-step reaction with 44 steps

1: 1.) nBu₂SnO, 2.) nBu₄NBr / 1.) MeOH, 60 deg C, 1 h, 2.) C₆H₆, 80 deg C, 5 h

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 18 h

4: benzene / 17 h / 25 °C

5: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

6: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

7: Et₃N, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 2 h

8: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1 h

9: TBAF / tetrahydrofuran / 1 h / -20 - 0 °C

10: imidazole / dimethylformamide; CH₂Cl₂ / 3 h / 0 °C

11: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 30 min

12: 1.) 9-BBN, 2.) H₂O₂, NaHCO₃, H₂O / 1.) THF, 0 deg C, 4 h, 2.) THF, 0 deg C, 4 h

13: SO₃*pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

14: benzene / 11 h / 25 °C

15: 88 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

16: 97 percent / 4 Angstroem molecular sieves, (+)-DET, Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 18 h / -25 °C

17: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

18: 1) NaHMDS / 1.) THF, 2.) THF, 0 deg C, 15 min

19: 26 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

20: imidazole / CH₂Cl₂ / 1 h / 0 °C

21: pyridinium p-toluenesulfonate, 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 25 °C

22: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 1 h, 2.) CH₂Cl₂, MeOH, 25 deg C, 2 h

23: pyridinium p-toluenesulfonate / CH₂Cl₂ / 28 h / 25 °C

24: TBAF / tetrahydrofuran / 3 h / 25 °C

25: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

26: toluene / 5 h / 25 °C

27: H₂ / Raney-Nickel W₂

28: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

29: imidazole / CH₂Cl₂ / 4 h / 25 °C

30: pyridinium p-toluenesulfonate / methanol / 6 h / 25 °C

31: imidazole / CH₂Cl₂ / 4.5 h / 0 °C

32: TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

33: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 - 0 °C

34: 91 percent / Et₃N, SO₃*py / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

35: 1.) n-BuLi, 2.) HMPA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 30 min; 25 deg C, 1 h

36: 83 percent / TBAF / tetrahydrofuran / 7 h / 25 °C

37: 92 percent / 4 Angstroem molecular sieves, NaHCO₃, AgClO₄ / nitromethane / 3 h / 25 °C

38: 94 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

39: 94 percent / AlMe₃ / toluene / 1 h / -78 °C

40: 92 percent / EtSH, Zn(OTf)2, NaHCO₃ / CH₂Cl₂ / 4 h / 25 °C

41: 92 percent / imidazole / CH₂Cl₂ / 1 h / 25 °C

42: 95 percent / 4-DMAP, Et₃N / CH₂Cl₂ / 2 h / 25 °C

43: H₂, Pd(OH)2/C / acetic acid / 48 h / 25 °C

44: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium dihydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; hydrogen; dihydrogen peroxide; trimethylaluminum; sodium hexamethyldisilazane; silver perchlorate; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; ethanethiol; Raney-Nickel W₂; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; nitromethane; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

Reference yield:

: 122821-83-4
2,6-Anhydro-4-O-benzyl-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-D-altro-non-8-enitol

: 221381-14-2
C₅₁H₈₄O₉Si₃

Guidance literature:: Multi-step reaction with 43 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

2: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 18 h

3: benzene / 17 h / 25 °C

4: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

5: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

6: Et₃N, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 2 h

7: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1 h

8: TBAF / tetrahydrofuran / 1 h / -20 - 0 °C

9: imidazole / dimethylformamide; CH₂Cl₂ / 3 h / 0 °C

10: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 30 min

11: 1.) 9-BBN, 2.) H₂O₂, NaHCO₃, H₂O / 1.) THF, 0 deg C, 4 h, 2.) THF, 0 deg C, 4 h

12: SO₃*pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

13: benzene / 11 h / 25 °C

14: 88 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

15: 97 percent / 4 Angstroem molecular sieves, (+)-DET, Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 18 h / -25 °C

16: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

17: 1) NaHMDS / 1.) THF, 2.) THF, 0 deg C, 15 min

18: 26 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

19: imidazole / CH₂Cl₂ / 1 h / 0 °C

20: pyridinium p-toluenesulfonate, 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 25 °C

21: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 1 h, 2.) CH₂Cl₂, MeOH, 25 deg C, 2 h

22: pyridinium p-toluenesulfonate / CH₂Cl₂ / 28 h / 25 °C

23: TBAF / tetrahydrofuran / 3 h / 25 °C

24: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

25: toluene / 5 h / 25 °C

26: H₂ / Raney-Nickel W₂

27: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

28: imidazole / CH₂Cl₂ / 4 h / 25 °C

29: pyridinium p-toluenesulfonate / methanol / 6 h / 25 °C

30: imidazole / CH₂Cl₂ / 4.5 h / 0 °C

31: TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

32: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 - 0 °C

33: 91 percent / Et₃N, SO₃*py / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

34: 1.) n-BuLi, 2.) HMPA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 30 min; 25 deg C, 1 h

35: 83 percent / TBAF / tetrahydrofuran / 7 h / 25 °C

36: 92 percent / 4 Angstroem molecular sieves, NaHCO₃, AgClO₄ / nitromethane / 3 h / 25 °C

37: 94 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

38: 94 percent / AlMe₃ / toluene / 1 h / -78 °C

39: 92 percent / EtSH, Zn(OTf)2, NaHCO₃ / CH₂Cl₂ / 4 h / 25 °C

40: 92 percent / imidazole / CH₂Cl₂ / 1 h / 25 °C

41: 95 percent / 4-DMAP, Et₃N / CH₂Cl₂ / 2 h / 25 °C

42: H₂, Pd(OH)2/C / acetic acid / 48 h / 25 °C

43: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium dihydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; trimethylaluminum; sodium hexamethyldisilazane; silver perchlorate; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; ethanethiol; Raney-Nickel W₂; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; nitromethane; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

Reference yield:

: 155434-13-2
(2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran

: 221381-14-2
C₅₁H₈₄O₉Si₃

Guidance literature:: Multi-step reaction with 42 steps

1: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 18 h

2: benzene / 17 h / 25 °C

3: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

4: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

5: Et₃N, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 2 h

6: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1 h

7: TBAF / tetrahydrofuran / 1 h / -20 - 0 °C

8: imidazole / dimethylformamide; CH₂Cl₂ / 3 h / 0 °C

9: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 30 min

10: 1.) 9-BBN, 2.) H₂O₂, NaHCO₃, H₂O / 1.) THF, 0 deg C, 4 h, 2.) THF, 0 deg C, 4 h

11: SO₃*pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

12: benzene / 11 h / 25 °C

13: 88 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

14: 97 percent / 4 Angstroem molecular sieves, (+)-DET, Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 18 h / -25 °C

15: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

16: 1) NaHMDS / 1.) THF, 2.) THF, 0 deg C, 15 min

17: 26 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

18: imidazole / CH₂Cl₂ / 1 h / 0 °C

19: pyridinium p-toluenesulfonate, 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 25 °C

20: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 1 h, 2.) CH₂Cl₂, MeOH, 25 deg C, 2 h

21: pyridinium p-toluenesulfonate / CH₂Cl₂ / 28 h / 25 °C

22: TBAF / tetrahydrofuran / 3 h / 25 °C

23: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

24: toluene / 5 h / 25 °C

25: H₂ / Raney-Nickel W₂

26: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

27: imidazole / CH₂Cl₂ / 4 h / 25 °C

28: pyridinium p-toluenesulfonate / methanol / 6 h / 25 °C

29: imidazole / CH₂Cl₂ / 4.5 h / 0 °C

30: TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

31: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 - 0 °C

32: 91 percent / Et₃N, SO₃*py / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

33: 1.) n-BuLi, 2.) HMPA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 30 min; 25 deg C, 1 h

34: 83 percent / TBAF / tetrahydrofuran / 7 h / 25 °C

35: 92 percent / 4 Angstroem molecular sieves, NaHCO₃, AgClO₄ / nitromethane / 3 h / 25 °C

36: 94 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

37: 94 percent / AlMe₃ / toluene / 1 h / -78 °C

38: 92 percent / EtSH, Zn(OTf)2, NaHCO₃ / CH₂Cl₂ / 4 h / 25 °C

39: 92 percent / imidazole / CH₂Cl₂ / 1 h / 25 °C

40: 95 percent / 4-DMAP, Et₃N / CH₂Cl₂ / 2 h / 25 °C

41: H₂, Pd(OH)2/C / acetic acid / 48 h / 25 °C

42: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium dihydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; trimethylaluminum; sodium hexamethyldisilazane; silver perchlorate; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; ethanethiol; Raney-Nickel W₂; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; nitromethane; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E