7-(3-benzyloxy-propyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol

Base Information

• Chemical Name: 7-(3-benzyloxy-propyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol
• CAS No.: 884004-92-6
• Molecular Formula: C₄₃H₇₈O₇Si₂
• Molecular Weight: 763.259

Synonyms:7-(3-benzyloxy-propyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol

Chemical Property of 7-(3-benzyloxy-propyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 7-(3-benzyloxy-propyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol

There total 21 articles about 7-(3-benzyloxy-propyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol 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: 85.0%

2-(3-benzyloxy-propyl)-4a,10a-dimethyl-4-(triisopropyl-silanyloxy)-7-[2-(triisopropyl-silanyloxy)-ethyl]-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracene (884004-90-4) → 7-(3-benzyloxy-propyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol (884004-92-6)

Guidance literature:

2-(3-benzyloxy-propyl)-4a,10a-dimethyl-4-(triisopropyl-silanyloxy)-7-[2-(triisopropyl-silanyloxy)-ethyl]-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracene; With borane-THF; In tetrahydrofuran; at 0 ℃; for 0.5h;

With water; dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Further stages.;

DOI:10.1002/chem.200500993

Reference yield:

C24H30O5 → 7-(3-benzyloxy-propyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol (884004-92-6)

Guidance literature:

Multi-step reaction with 17 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: 100 percent / (i-Pr)2NEt; DMAP / dimethylformamide / 14 h / 65 °C

12: NaBH₄ / ethanol / 4 h / -65 - 20 °C

13: 4.41 g / 1,3-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 1 h / 20 °C

14: TiCl₄; TMEDA; Zn / PbCl₂ / CH₂Cl₂; tetrahydrofuran / 2.7 h / Heating

15: 2.5 g / PhCH=RuCH{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 50 h / 20 °C

16: dimethyldioxirane / CH₂Cl₂ / 1 h / -78 - 0 °C

17: 0.431 g / DIBAL-H / CH₂Cl₂; hexane / 0.08 h / -78 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; water; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; 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; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 9: Mitsunobu inversion;

DOI:10.1002/chem.200500993

Reference yield:

C30H40O5 → 7-(3-benzyloxy-propyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol (884004-92-6)

Guidance literature:

Multi-step reaction with 14 steps

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

2: 92 percent / m-CPBA

3: 78 percent / NaH / tetrahydrofuran

4: PPTS; pyridine / toluene / 100 °C

5: 97 percent / DDQ; H₂O / CH₂Cl₂

6: DEAD; PPh₃ / toluene

7: NaOH / tetrahydrofuran; methanol

8: 100 percent / (i-Pr)2NEt; DMAP / dimethylformamide / 14 h / 65 °C

9: NaBH₄ / ethanol / 4 h / -65 - 20 °C

10: 4.41 g / 1,3-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 1 h / 20 °C

11: TiCl₄; TMEDA; Zn / PbCl₂ / CH₂Cl₂; tetrahydrofuran / 2.7 h / Heating

12: 2.5 g / PhCH=RuCH{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 50 h / 20 °C

13: dimethyldioxirane / CH₂Cl₂ / 1 h / -78 - 0 °C

14: 0.431 g / DIBAL-H / CH₂Cl₂; hexane / 0.08 h / -78 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; water; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; 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; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 6: Mitsunobu inversion;

DOI:10.1002/chem.200500993

upstream raw materials:

2-(3-benzyloxy-propyl)-4a,10a-dimethyl-4-(triisopropyl-silanyloxy)-7-[2-(triisopropyl-silanyloxy)-ethyl]-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracene

2-allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-(triisopropyl-silanyloxy)-hexahydro-pyrano[3,2-b]pyran-3-one

3-(triisopropyl-silanyloxy)-propionic acid 2-allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-(triisopropyl-silanyloxy)-octahydro-pyrano[3,2-b]pyran-3-yl ester

triisopropylsilyl trifluoromethanesulfonate

Downstream raw materials:

7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol

7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(2-hydroxy-ethyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-decahydro-1,8,10-trioxa-anthracen-3-ol

C₅₅H₉₈O₇Si₄

2-[7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-4a,10a-dimethyl-3-(triethyl-silanyloxy)-5-(triisopropyl-silanyloxy)-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol

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