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

Base Information

• Chemical Name: 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
• CAS No.: 884005-06-5
• Molecular Formula: C₄₂H₇₆O₈Si₃
• Molecular Weight: 793.317

Synonyms: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

Chemical Property of 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

Chemical Property:

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• Pictogram(s):  
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MSDS Files:

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Technology Process of 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

There total 19 articles about 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 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: 96.0%

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 (884005-20-3) + t-butyldimethylsiyl triflate (69739-34-0) → 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 (884005-06-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1002/chem.200500993

Reference yield:

C30H48O7Si → 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 (884005-06-5)

Guidance literature:

Multi-step reaction with 16 steps

1.1: DIBAL-H

2.1: 100 percent / HF*pyridine / tetrahydrofuran / 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / -65 °C

4.1: 2,6-lutidine / 0 °C

5.1: 88 percent / CuI / diethyl ether / -40 - 20 °C

6.1: 85 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

7.1: 95 percent / DCC; DMAP / CH₂Cl₂ / 4 h / 20 °C

8.1: 100 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 3 h / 20 °C

9.1: 71 percent / TiCl₄; Zn; TMEDA / PbCl₂ / tetrahydrofuran / 65 °C

10.1: 88 percent / Schrock's molybdenum catalyst / hexane / 16 h / 50 °C

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

12.1: 0.222 g / DIBAL-H / CH₂Cl₂; hexane / 0.2 h / -70 °C

13.1: 90 percent / NMO; TPAP / CH₂Cl₂ / 1.5 h / 20 °C

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

14.2: 90 percent / Pd(OAc)2 / acetonitrile / 2 h / 20 °C

15.1: 94 percent / toluene; diethyl ether / 0.5 h / -70 °C

16.1: 96 percent / Et₃N / CH₂Cl₂ / 1.5 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; pyridine hydrogenfluoride; 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; toluene; 14.2: Saegusa oxidation;

DOI:10.1002/chem.200500993

Reference yield:

C22H34O7 → 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 (884005-06-5)

Guidance literature:

Multi-step reaction with 14 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

13.1: 94 percent / toluene; diethyl ether / 0.5 h / -70 °C

14.1: 96 percent / Et₃N / CH₂Cl₂ / 1.5 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; toluene; 12.2: Saegusa oxidation;

DOI:10.1002/chem.200500993

upstream 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

t-butyldimethylsiyl triflate

C₃₃H₅₂O₈S₂Si

C₂₅H₃₈O₆

Downstream raw materials:

C₇₁H₁₁₆O₁₄Si₃

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