[2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane

Base Information

• Chemical Name: [2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane
• CAS No.: 884004-84-6
• Molecular Formula: C₂₆H₄₀O₅Si
• Molecular Weight: 460.686
• Mol file: 884004-84-6.mol

Synonyms:[2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane

Chemical Property of [2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane

There total 18 articles about [2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane 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: 95.0%

C28H44O5Si (884004-83-5) → [2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane (884004-84-6)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In benzene; at 20 ℃; for 8h;

DOI:10.1002/chem.200500993

Reference yield:

C24H30O5 → [2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane (884004-84-6)

Guidance literature:

Multi-step reaction with 15 steps

1: 6.5 g / diethyl ether / 0.5 h / -65 - 20 °C

2: 85 percent / (i-Pr)2NEt

3: TiCl₄; TMEDA; Zn / PbCl₂ / CH₂Cl₂

4: PhCH=RuCH{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 20 °C

5: 92 percent / m-CPBA

6: 78 percent / NaH / tetrahydrofuran

7: PPTS; pyridine / toluene / 100 °C

8: 97 percent / DDQ; H₂O / CH₂Cl₂

9: DEAD; PPh₃ / toluene

10: NaOH / tetrahydrofuran; methanol

11: 97 percent / NEt₃ / dimethylformamide

12: 97 percent / NaBH₄ / ethanol / 2 h / -65 - 20 °C

13: 95 percent / TsOH*H₂O / various solvent(s) / 0.5 h / 0 °C

14: 98 percent / NEt₃; TMSOTf / CH₂Cl₂ / 1 h / -60 - 0 °C

15: 95 percent / PhCH=Ru{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 8 h / 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate; water; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(II) chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 9: Mitsunobu inversion;

DOI:10.1002/chem.200500993

Reference yield:

C16H20O3 → [2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane (884004-84-6)

Guidance literature:

Multi-step reaction with 18 steps

1: NaBH₄; CeCl₃*7H₂O / methanol / 0 °C

2: NaH / dimethylformamide

3: dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / -65 - 20 °C

4: 6.5 g / diethyl ether / 0.5 h / -65 - 20 °C

5: 85 percent / (i-Pr)2NEt

6: TiCl₄; TMEDA; Zn / PbCl₂ / CH₂Cl₂

7: PhCH=RuCH{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 20 °C

8: 92 percent / m-CPBA

9: 78 percent / NaH / tetrahydrofuran

10: PPTS; pyridine / toluene / 100 °C

11: 97 percent / DDQ; H₂O / CH₂Cl₂

12: DEAD; PPh₃ / toluene

13: NaOH / tetrahydrofuran; methanol

14: 97 percent / NEt₃ / dimethylformamide

15: 97 percent / NaBH₄ / ethanol / 2 h / -65 - 20 °C

16: 95 percent / TsOH*H₂O / various solvent(s) / 0.5 h / 0 °C

17: 98 percent / NEt₃; TMSOTf / CH₂Cl₂ / 1 h / -60 - 0 °C

18: 95 percent / PhCH=Ru{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 8 h / 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate; water; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(II) chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene; 1: Luche reduction / 12: Mitsunobu inversion;

DOI:10.1002/chem.200500993

upstream raw materials:

C₂₈H₄₄O₅Si

(2S,4R)-2-(3-Benzyloxy-propyl)-5-methyl-3,4-dihydro-2H-pyran-4-ol

(2S,4R)-2-(3-Benzyloxy-propyl)-4-(4-methoxy-benzyloxy)-5-methyl-3,4-dihydro-2H-pyran

(2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

Downstream raw materials:

C₂₆H₄₀O₆Si

C₂₆H₄₂O₆Si