(1R,2S,4S,6S,8S)-6-(3,4-Dimethoxy-phenyl)-8-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]nonane

Base Information

• Chemical Name: (1R,2S,4S,6S,8S)-6-(3,4-Dimethoxy-phenyl)-8-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]nonane
• CAS No.: 401612-68-8
• Molecular Formula: C₂₈H₄₆O₈Si₂
• Molecular Weight: 566.839
• Mol file: 401612-68-8.mol

Synonyms:(1R,2S,4S,6S,8S)-6-(3,4-Dimethoxy-phenyl)-8-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]nonane

Chemical Property of (1R,2S,4S,6S,8S)-6-(3,4-Dimethoxy-phenyl)-8-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,4S,6S,8S)-6-(3,4-Dimethoxy-phenyl)-8-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]nonane

There total 11 articles about (1R,2S,4S,6S,8S)-6-(3,4-Dimethoxy-phenyl)-8-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]nonane 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: 74.0%

(1R,2R,3S,5S,7S)-5-(3,4-Dimethoxy-phenyl)-7-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol (401612-67-7) → (1R,2S,4S,6S,8S)-6-(3,4-Dimethoxy-phenyl)-8-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-3,7,9-trioxa-tricyclo[4.2.1.02,4]nonane (401612-68-8)

Guidance literature:

(1R,2R,3S,5S,7S)-5-(3,4-Dimethoxy-phenyl)-7-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol; With dmap; triethylamine; p-toluenesulfonyl chloride; In dichloromethane;

With sodium methylate; In methanol;

DOI:10.1016/S0040-4039(01)01912-8

Reference yield:

1,2-dimethoxybenzene (91-16-7) → (1R,2S,4S,6S,8S)-6-(3,4-Dimethoxy-phenyl)-8-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-3,7,9-trioxa-tricyclo[4.2.1.02,4]nonane (401612-68-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 75 percent / AlCl₃ / CH₂Cl₂ / 3 h / 0 °C

2.1: 90 percent / camphorsulfonic acid / benzene / 12 h / Heating

3.1: o-NO₂C₆H₄SeCN; NaBH₄ / ethanol / 20 °C

3.2: 96 percent / aq. H₂O₂ / tetrahydrofuran / 20 °C

4.1: 93 percent / Cl₂(PCy₃)2Ru=CHPh; air; Et₃N / CH₂Cl₂ / 7 h

5.1: 94 percent / K₃Fe(CN)6; (DHQ)2AQN; K₂CO₃ / OsO₄ / 2-methyl-propan-2-ol; H₂O / 31 h / 0 °C

6.1: Et₃N; Bu₂SnO / CH₂Cl₂ / 16 h / 20 °C

6.2: 4-dimethylaminopyridine; Et₃N; Bu₂SnO / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 1.16 g / 18-crown-6; 4 Angstroem molecular sieves / toluene / Heating

8.1: 99 percent / MeONa / methanol / 4 h / 20 °C

9.1: 90 percent / imidazole / dimethylformamide / 2.5 h / 20 °C

10.1: TsCl; Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / 20 °C

10.2: 74 percent / MeONa / methanol / 0.5 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; Grubbs catalyst first generation; aluminium trichloride; ortho-nitrophenyl selenocyanate; (DHQ)2AQN; air; 18-crown-6 ether; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; di(n-butyl)tin oxide; potassium carbonate; triethylamine; p-toluenesulfonyl chloride; potassium hexacyanoferrate(III); osmium(VIII) oxide; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 1.1: Friedel-Crafts reaction;

DOI:10.1021/jo0263014

Reference yield:

4-Brom-3',4'-dimethoxybutyrophenon (105174-48-9) → (1R,2S,4S,6S,8S)-6-(3,4-Dimethoxy-phenyl)-8-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-3,7,9-trioxa-tricyclo[4.2.1.02,4]nonane (401612-68-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / camphorsulfonic acid / benzene / 12 h / Heating

2.1: o-NO₂C₆H₄SeCN; NaBH₄ / ethanol / 20 °C

2.2: 96 percent / aq. H₂O₂ / tetrahydrofuran / 20 °C

3.1: 93 percent / Cl₂(PCy₃)2Ru=CHPh; air; Et₃N / CH₂Cl₂ / 7 h

4.1: 94 percent / K₃Fe(CN)6; (DHQ)2AQN; K₂CO₃ / OsO₄ / 2-methyl-propan-2-ol; H₂O / 31 h / 0 °C

5.1: Et₃N; Bu₂SnO / CH₂Cl₂ / 16 h / 20 °C

5.2: 4-dimethylaminopyridine; Et₃N; Bu₂SnO / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 1.16 g / 18-crown-6; 4 Angstroem molecular sieves / toluene / Heating

7.1: 99 percent / MeONa / methanol / 4 h / 20 °C

8.1: 90 percent / imidazole / dimethylformamide / 2.5 h / 20 °C

9.1: TsCl; Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / 20 °C

9.2: 74 percent / MeONa / methanol / 0.5 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; Grubbs catalyst first generation; ortho-nitrophenyl selenocyanate; (DHQ)2AQN; air; 18-crown-6 ether; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; di(n-butyl)tin oxide; potassium carbonate; triethylamine; p-toluenesulfonyl chloride; potassium hexacyanoferrate(III); osmium(VIII) oxide; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/jo0263014

upstream raw materials:

(1R,2R,3S,5S,7S)-5-(3,4-Dimethoxy-phenyl)-7-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol

1,2-dimethoxybenzene

4-Brom-3',4'-dimethoxybutyrophenon

(1R,5R,7R)-5-(3,4-Dimethoxy-phenyl)-7-vinyl-6,8-dioxa-bicyclo[3.2.1]oct-2-ene

Downstream raw materials:

Acetic acid (2S,4S,5R,6R)-5-azido-2-(3,4-dimethoxy-phenyl)-2-methoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-4-yl ester

(1R,2R,3S,5S,7S)-2-Azido-5-(3,4-dimethoxy-phenyl)-7-((R)-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilepan-6-yl)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol