C₅₃H₆₆O₁₆Si

Base Information

Chemical Name:C₅₃H₆₆O₁₆Si
CAS No.:306726-54-5
Molecular Formula:C₅₃H₆₆O₁₆Si
Molecular Weight:987.183
Hs Code.:

C<sub>53</sub>H<sub>66</sub>O<sub>16</sub>Si

Synonyms:C₅₃H₆₆O₁₆Si

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Chemical Property of C₅₃H₆₆O₁₆Si

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Technology Process of C₅₃H₆₆O₁₆Si

There total 53 articles about C₅₃H₆₆O₁₆Si 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:

: 306726-10-3
(1R,2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butan-1-ol

: 306726-54-5
C₅₃H₆₆O₁₆Si

Guidance literature:: Multi-step reaction with 29 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

2.1: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / 25 °C

3.1: NaBH₄ / methanol / 0.5 h / 0 °C

3.2: H₂O; CuCl₂; CuO / acetonitrile / 2 h / 25 °C

4.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

5.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

6.1: nBu₂SnO / methanol / 3 h / Heating

6.2: TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

6.3: 10.82 g / PPTS; MeOH / 1 h / 25 °C

7.1: 87 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

8.1: 95 percent / NaOH; MeOH / diethyl ether / 1 h / 25 °C

9.1: NaH / dimethylformamide / 0.08 h / 0 °C

9.2: 90 percent / nBu₄NI / dimethylformamide / 4 h / 0 - 25 °C

10.1: 91 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

11.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

12.1: DABCO / [(Ph₃P)3RhCl] / aq. ethanol / 2 h / Heating

13.1: 9.27 g / NMO; OsO₄; H₂O / acetone / 8 h / 25 °C

14.1: nBu₂SnO / toluene / 3 h / Heating

14.2: toluene / 1 h / 0 - 25 °C

15.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

16.1: 96 percent / Et₃N; MeOH / CH₂Cl₂ / 6 h / 40 °C

17.1: 92 percent / SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 - 25 °C

18.1: 98 percent / K₂CO₃; MeOH / diethyl ether / 12 h / 25 °C

19.1: aq. NaIO₄; NaHCO₃ / methanol; CH₂Cl₂ / 2 h / 25 °C

20.1: 430 mg / iPr₂NH; vinyl acetate / toluene / 12 h / 140 °C

21.1: 95 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

22.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

23.1: 95 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 25 °C

24.1: 85 percent / Martin sulfurane; Et₃N / CHCl₃ / 2 h / 50 °C

25.1: 90 percent / K₂CO₃; MeOH / 6 h / 25 °C

26.1: NaH; 18-crown-6 / tetrahydrofuran / 0.25 h / 0 °C

26.2: 80 percent / tetrahydrofuran / 2 h / 0 °C

27.1: NMO; H₂O; OsO₄ / quinuclidine / acetone / 36 h / 25 °C

28.1: nBu₂SnO / methanol / 3 h / Heating

28.2: dioxane / 0.5 h / 15 °C

29.1: 85 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; methanol; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; vinyl acetate; N-methyl-2-indolinone; Martins sulfurane; 18-crown-6 ether; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tin(ll) chloride; Quinuclidine; Wilkinson's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: Esterification / 2.1: Methylation / 3.1: Reduction / 3.2: Ring cleavage / 4.1: Cyclization / 5.1: Addition / 6.1: Cyclization / 6.2: Ring cleavage / 6.3: Methanolysis / 7.1: Methylation / 8.1: Debenzoylation / 9.1: Metallation / 9.2: Etherification / 10.1: Oxidation / 11.1: Etherification / 12.1: Isomerization / 13.1: Oxidation / 14.1: Cyclization / 14.2: Ring cleavage / 15.1: Esterification / 16.1: Deacylation / 17.1: Glycosidation / 18.1: Debenzoylation / 19.1: Oxidation / 20.1: Cyclizati;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 256341-86-3
tert-Butyl-[(3S,4S,5R)-2-fluoro-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yloxy]-dimethyl-silane

: 306726-54-5
C₅₃H₆₆O₁₆Si

Guidance literature:: Multi-step reaction with 13 steps

1.1: 92 percent / SnCl₂ / diethyl ether / 3 h / 0 - 25 °C

2.1: 98 percent / K₂CO₃; MeOH / diethyl ether / 1 h / 25 °C

3.1: aq. NaIO₄; NaHCO₃ / methanol; CH₂Cl₂ / 2 h / 25 °C

4.1: 430 mg / iPr₂NH; vinyl acetate / toluene / 12 h / 140 °C

5.1: 95 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

6.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

7.1: 95 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 25 °C

8.1: 85 percent / Martin sulfurane; Et₃N / CHCl₃ / 2 h / 50 °C

9.1: 90 percent / K₂CO₃; MeOH / 6 h / 25 °C

10.1: NaH; 18-crown-6 / tetrahydrofuran / 0.25 h / 0 °C

10.2: 80 percent / tetrahydrofuran / 2 h / 0 °C

11.1: NMO; H₂O; OsO₄ / quinuclidine / acetone / 36 h / 25 °C

12.1: nBu₂SnO / methanol / 3 h / Heating

12.2: dioxane / 0.5 h / 15 °C

13.1: 85 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 25 °C

With methanol; dmap; sodium periodate; osmium(VIII) oxide; vinyl acetate; N-methyl-2-indolinone; Martins sulfurane; 18-crown-6 ether; tetrabutyl ammonium fluoride; water; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; triethylamine; diisopropylamine; tin(ll) chloride; Quinuclidine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; acetone; toluene; 1.1: Glycosidation / 2.1: Deacylation / 3.1: Oxidation / 4.1: Cyclization / 5.1: Silyl ether cleavage / 6.1: Esterification / 7.1: Silyl ether cleavage / 8.1: Dehydration / 9.1: Debenzoylation / 10.1: Metallation / 10.2: Etherification / 11.1: Oxidation / 12.1: Cyclization / 12.2: Ring cleavage / 13.1: Oxidation;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 306726-12-5
Benzoic acid (1R,2R,3S)-2,3-bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butyl ester

: 306726-54-5
C₅₃H₆₆O₁₆Si

Guidance literature:: Multi-step reaction with 28 steps

1.1: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / 25 °C

2.1: NaBH₄ / methanol / 0.5 h / 0 °C

2.2: H₂O; CuCl₂; CuO / acetonitrile / 2 h / 25 °C

3.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

4.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

5.1: nBu₂SnO / methanol / 3 h / Heating

5.2: TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

5.3: 10.82 g / PPTS; MeOH / 1 h / 25 °C

6.1: 87 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

7.1: 95 percent / NaOH; MeOH / diethyl ether / 1 h / 25 °C

8.1: NaH / dimethylformamide / 0.08 h / 0 °C

8.2: 90 percent / nBu₄NI / dimethylformamide / 4 h / 0 - 25 °C

9.1: 91 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

10.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

11.1: DABCO / [(Ph₃P)3RhCl] / aq. ethanol / 2 h / Heating

12.1: 9.27 g / NMO; OsO₄; H₂O / acetone / 8 h / 25 °C

13.1: nBu₂SnO / toluene / 3 h / Heating

13.2: toluene / 1 h / 0 - 25 °C

14.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

15.1: 96 percent / Et₃N; MeOH / CH₂Cl₂ / 6 h / 40 °C

16.1: 92 percent / SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 - 25 °C

17.1: 98 percent / K₂CO₃; MeOH / diethyl ether / 12 h / 25 °C

18.1: aq. NaIO₄; NaHCO₃ / methanol; CH₂Cl₂ / 2 h / 25 °C

19.1: 430 mg / iPr₂NH; vinyl acetate / toluene / 12 h / 140 °C

20.1: 95 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

21.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

22.1: 95 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 25 °C

23.1: 85 percent / Martin sulfurane; Et₃N / CHCl₃ / 2 h / 50 °C

24.1: 90 percent / K₂CO₃; MeOH / 6 h / 25 °C

25.1: NaH; 18-crown-6 / tetrahydrofuran / 0.25 h / 0 °C

25.2: 80 percent / tetrahydrofuran / 2 h / 0 °C

26.1: NMO; H₂O; OsO₄ / quinuclidine / acetone / 36 h / 25 °C

27.1: nBu₂SnO / methanol / 3 h / Heating

27.2: dioxane / 0.5 h / 15 °C

28.1: 85 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; methanol; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; vinyl acetate; N-methyl-2-indolinone; Martins sulfurane; 18-crown-6 ether; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tin(ll) chloride; Quinuclidine; Wilkinson's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: Methylation / 2.1: Reduction / 2.2: Ring cleavage / 3.1: Cyclization / 4.1: Addition / 5.1: Cyclization / 5.2: Ring cleavage / 5.3: Methanolysis / 6.1: Methylation / 7.1: Debenzoylation / 8.1: Metallation / 8.2: Etherification / 9.1: Oxidation / 10.1: Etherification / 11.1: Isomerization / 12.1: Oxidation / 13.1: Cyclization / 13.2: Ring cleavage / 14.1: Esterification / 15.1: Deacylation / 16.1: Glycosidation / 17.1: Debenzoylation / 18.1: Oxidation / 19.1: Cyclization / 20.1: Silyl ether;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8