(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

Base Information

• Chemical Name: (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
• CAS No.: 401612-65-5
• Molecular Formula: C₂₈H₄₇N₃O₈Si₂
• Molecular Weight: 609.867
• Mol file: 401612-65-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 12 articles about (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 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: 59.0%

(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) → (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 (401612-65-5)

Guidance literature:

With sodium azide; magnesium sulfate; In N,N-dimethyl-formamide; at 90 - 95 ℃;

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

Reference yield:

1,2-dimethoxybenzene (91-16-7) → (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 (401612-65-5)

Guidance literature:

Multi-step reaction with 11 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

11.1: 59 percent / NaN₃; MgSO₄ / dimethylformamide / 20 h / 90 - 95 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; Grubbs catalyst first generation; aluminium trichloride; sodium azide; 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; magnesium sulfate; 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,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 (401612-65-5)

Guidance literature:

Multi-step reaction with 10 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

10.1: 59 percent / NaN₃; MgSO₄ / dimethylformamide / 20 h / 90 - 95 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; Grubbs catalyst first generation; sodium azide; 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; magnesium sulfate; 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,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

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