2H-Pyran-2-ol, 6-[(1R)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-(phenylmethoxy)ethyl]- 2-ethenyltetrahydro-5-methoxy-, (2S,5S,6S)-

Base Information

• Chemical Name: 2H-Pyran-2-ol, 6-[(1R)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-(phenylmethoxy)ethyl]- 2-ethenyltetrahydro-5-methoxy-, (2S,5S,6S)-
• CAS No.: 855127-40-1
• Molecular Formula: C₃₃H₄₂O₅Si
• Molecular Weight: 546.779
• Mol file: 855127-40-1.mol

Synonyms:

Chemical Property of 2H-Pyran-2-ol, 6-[(1R)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-(phenylmethoxy)ethyl]- 2-ethenyltetrahydro-5-methoxy-, (2S,5S,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran-2-ol, 6-[(1R)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-(phenylmethoxy)ethyl]- 2-ethenyltetrahydro-5-methoxy-, (2S,5S,6S)-

There total 14 articles about 2H-Pyran-2-ol, 6-[(1R)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-(phenylmethoxy)ethyl]- 2-ethenyltetrahydro-5-methoxy-, (2S,5S,6S)- 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) + vinyl magnesium bromide (1826-67-1) → (2S,5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-2-vinyl-tetrahydro-pyran-2-ol (855127-40-1)

Guidance literature:

In diethyl ether; at -78 ℃; for 1h;

DOI:10.1021/ol050653q DOI:10.1016/j.tet.2006.06.113

Reference yield:

(2R,3S)-2-Benzyloxy-pent-4-ene-1,3-diol (855127-45-6) → (2S,5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-2-vinyl-tetrahydro-pyran-2-ol (855127-40-1)

Guidance literature:

Multi-step reaction with 12 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

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; 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) → (2S,5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-2-vinyl-tetrahydro-pyran-2-ol (855127-40-1)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/ol050653q

upstream raw materials:

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

vinyl magnesium bromide

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

(2R,3S,4S)-2-Benzyloxy-4-methoxy-hept-6-ene-1,3-diol

Downstream raw materials:

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

[(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