9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,10a,11,11a-octahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one

Base Information

• Chemical Name: 9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,10a,11,11a-octahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one
• CAS No.: 884005-05-4
• Molecular Formula: C₃₅H₅₈O₈Si₂
• Molecular Weight: 663.012

Synonyms:9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,10a,11,11a-octahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one

Chemical Property of 9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,10a,11,11a-octahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one

Chemical Property:

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Technology Process of 9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,10a,11,11a-octahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one

There total 17 articles about 9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,10a,11,11a-octahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one 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: 90.0%

9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one (884005-19-0) → 9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,10a,11,11a-octahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one (884005-05-4)

Guidance literature:

9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one; With chloro-trimethyl-silane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; at -70 ℃; for 1h; pH=7.4;

palladium diacetate; In acetonitrile; at 20 ℃; for 2h; Further stages.;

DOI:10.1002/chem.200500993

Reference yield:

C22H34O7 → 9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,10a,11,11a-octahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one (884005-05-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 2,6-lutidine / CH₂Cl₂ / -65 °C

2.1: 2,6-lutidine / 0 °C

3.1: 88 percent / CuI / diethyl ether / -40 - 20 °C

4.1: 85 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

5.1: 95 percent / DCC; DMAP / CH₂Cl₂ / 4 h / 20 °C

6.1: 100 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 3 h / 20 °C

7.1: 71 percent / TiCl₄; Zn; TMEDA / PbCl₂ / tetrahydrofuran / 65 °C

8.1: 88 percent / Schrock's molybdenum catalyst / hexane / 16 h / 50 °C

9.1: dimethyldioxirane / CH₂Cl₂; acetone / -70 - 0 °C

10.1: 0.222 g / DIBAL-H / CH₂Cl₂; hexane / 0.2 h / -70 °C

11.1: 90 percent / NMO; TPAP / CH₂Cl₂ / 1.5 h / 20 °C

12.1: Et₃N; TMSCl; LiHMDS / tetrahydrofuran / 1 h / -70 °C / pH 7.4

12.2: 90 percent / Pd(OAc)2 / acetonitrile / 2 h / 20 °C

With 2,6-dimethylpyridine; dmap; copper(l) iodide; chloro-trimethyl-silane; N-methyl-2-indolinone; tetrapropylammonium perruthennate; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; titanium tetrachloride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; zinc; bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum; lead(II) chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone; 12.2: Saegusa oxidation;

DOI:10.1002/chem.200500993

Reference yield:

C33H52O8S2Si (511256-96-5) → 9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,10a,11,11a-octahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one (884005-05-4)

Guidance literature:

Multi-step reaction with 17 steps

1.1: Bu₃SnH; AIBN / benzene / 1.5 h / 80 °C

1.2: 83 percent / TiCl₄; Zn; TMEDA / PbCl₂ / tetrahydrofuran / 65 °C

2.1: 83 percent / PhCH=RuCH{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 80 °C

3.1: dimethyldioxirane

4.1: DIBAL-H

5.1: 100 percent / HF*pyridine / tetrahydrofuran / 0 °C

6.1: 2,6-lutidine / CH₂Cl₂ / -65 °C

7.1: 2,6-lutidine / 0 °C

8.1: 88 percent / CuI / diethyl ether / -40 - 20 °C

9.1: 85 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

10.1: 95 percent / DCC; DMAP / CH₂Cl₂ / 4 h / 20 °C

11.1: 100 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 3 h / 20 °C

12.1: 71 percent / TiCl₄; Zn; TMEDA / PbCl₂ / tetrahydrofuran / 65 °C

13.1: 88 percent / Schrock's molybdenum catalyst / hexane / 16 h / 50 °C

14.1: dimethyldioxirane / CH₂Cl₂; acetone / -70 - 0 °C

15.1: 0.222 g / DIBAL-H / CH₂Cl₂; hexane / 0.2 h / -70 °C

16.1: 90 percent / NMO; TPAP / CH₂Cl₂ / 1.5 h / 20 °C

17.1: Et₃N; TMSCl; LiHMDS / tetrahydrofuran / 1 h / -70 °C / pH 7.4

17.2: 90 percent / Pd(OAc)2 / acetonitrile / 2 h / 20 °C

With 2,6-dimethylpyridine; dmap; copper(l) iodide; chloro-trimethyl-silane; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; titanium tetrachloride; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum; lead(II) chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone; benzene; 17.2: Saegusa oxidation;

DOI:10.1002/chem.200500993

upstream raw materials:

9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-3-(trimethyl-silanyloxy)-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one

C₃₃H₅₂O₈S₂Si

C₂₅H₃₈O₆

(tert-butyl-dimethyl-silanyloxy)-acetic acid 2-but-3-enyl-7-hydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yl ester

Downstream raw materials:

9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a,8-trimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

8-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a,8-trimethyl-3-(trimethyl-silanyloxy)-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

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