[(R)-2-Benzyloxy-2-((2S,3S,6R)-6-but-3-enyloxy-3-methoxy-6-vinyl-tetrahydro-pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: [(R)-2-Benzyloxy-2-((2S,3S,6R)-6-but-3-enyloxy-3-methoxy-6-vinyl-tetrahydro-pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane
• CAS No.: 855127-50-3
• Molecular Formula: C₃₇H₄₈O₅Si
• Molecular Weight: 600.871
• Mol file: 855127-50-3.mol

Synonyms:[(R)-2-Benzyloxy-2-((2S,3S,6R)-6-but-3-enyloxy-3-methoxy-6-vinyl-tetrahydro-pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane

Chemical Property of [(R)-2-Benzyloxy-2-((2S,3S,6R)-6-but-3-enyloxy-3-methoxy-6-vinyl-tetrahydro-pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(R)-2-Benzyloxy-2-((2S,3S,6R)-6-but-3-enyloxy-3-methoxy-6-vinyl-tetrahydro-pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane

There total 15 articles about [(R)-2-Benzyloxy-2-((2S,3S,6R)-6-but-3-enyloxy-3-methoxy-6-vinyl-tetrahydro-pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane 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:

(5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-tetrahydro-pyran-2-one (855127-41-2) → [(R)-2-Benzyloxy-2-((2S,3S,6R)-6-but-3-enyloxy-3-methoxy-6-vinyl-tetrahydro-pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane (855127-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent Turnov_. / diethyl ether / 1 h / -78 °C

2: 89 percent / Tf₂NH / CH₂Cl₂ / 0.08 h / -78 °C

With bis(trifluoromethanesulfonyl)amide; In diethyl ether; dichloromethane;

DOI:10.1016/j.tet.2006.06.113

Reference yield:

(2R,3S)-2-Benzyloxy-pent-4-ene-1,3-diol (855127-45-6) → [(R)-2-Benzyloxy-2-((2S,3S,6R)-6-but-3-enyloxy-3-methoxy-6-vinyl-tetrahydro-pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane (855127-50-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: imidazole / dimethylformamide / 12 h / 20 °C

2.1: 100 percent / K₂OsO₄*H₂O; NMO / acetone; H₂O / 48 h / 20 °C

3.1: 74 percent Turnov_. / NaIO₄ / tetrahydrofuran; H₂O / -10 - 20 °C

4.1: 95 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / -78 °C

5.1: 85 percent / proton sponge; molecular sieves 4 Angstroem / CH₂Cl₂ / 24 h / 20 °C

6.1: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

7.1: 99 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

8.1: BH₃*Me₂S / hexane / 12 h / 20 °C

8.2: 78 percent / NaOH; H₂O₂ / H₂O; hexane; ethanol / 1 h / 20 °C

9.1: 1.73 g / TEMPO; BAIB / CH₂Cl₂ / 12 h / 20 °C

10.1: tetra-n-butylammonium fluoride / tetrahydrofuran / -10 - 20 °C

11.1: 223.0 mg / imidazole / CH₂Cl₂ / 3 h / 20 °C

12.1: 73 percent Turnov_. / diethyl ether / 1 h / -78 °C

13.1: 89 percent / molecular sieves 4 Angstroem; Tf₂NH / CH₂Cl₂ / 0.08 h / -78 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium osmate(VI); sodium periodate; N-methyl-2-indolinone; Proton Sponge; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; bis(trifluoromethanesulfonyl)amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ol050653q

Reference yield:

(2R,3S,4S)-2-Benzyloxy-4-methoxy-hept-6-ene-1,3-diol (855127-54-7) → [(R)-2-Benzyloxy-2-((2S,3S,6R)-6-but-3-enyloxy-3-methoxy-6-vinyl-tetrahydro-pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane (855127-50-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

2.1: BH₃*Me₂S / hexane / 12 h / 20 °C

2.2: 78 percent / NaOH; H₂O₂ / H₂O; hexane; ethanol / 1 h / 20 °C

3.1: 1.73 g / TEMPO; BAIB / CH₂Cl₂ / 12 h / 20 °C

4.1: tetra-n-butylammonium fluoride / tetrahydrofuran / -10 - 20 °C

5.1: 223.0 mg / imidazole / CH₂Cl₂ / 3 h / 20 °C

6.1: 73 percent Turnov_. / diethyl ether / 1 h / -78 °C

7.1: 89 percent / molecular sieves 4 Angstroem; Tf₂NH / CH₂Cl₂ / 0.08 h / -78 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; bis(trifluoromethanesulfonyl)amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ol050653q

upstream raw materials:

(2S,5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-2-vinyl-tetrahydro-pyran-2-ol

homoalylic alcohol

(5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-tetrahydro-pyran-2-one

(2R,3S)-2-Benzyloxy-pent-4-ene-1,3-diol

Downstream raw materials:

[(R)-2-Benzyloxy-2-((2S,3S,6R)-3-methoxy-6-{(1R,2S)-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-methyl-but-3-enyloxy}-6-vinyl-tetrahydro-pyran-2-yl)-ethoxy]-tert-butyl-diphenyl-silane