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

Base Information

• Chemical Name: (5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-tetrahydro-pyran-2-one
• CAS No.: 855127-41-2
• Molecular Formula: C₃₁H₃₈O₅Si
• Molecular Weight: 518.725
• Mol file: 855127-41-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-tetrahydro-pyran-2-one 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-hydroxy-ethyl)-5-methoxy-tetrahydro-pyran-2-one + tert-butylchlorodiphenylsilane (58479-61-1) → (5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-tetrahydro-pyran-2-one (855127-41-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ol050653q

Reference yield:

(2R,3S)-2-Benzyloxy-pent-4-ene-1,3-diol (855127-45-6) → (5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-tetrahydro-pyran-2-one (855127-41-2)

Guidance literature:

Multi-step reaction with 11 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

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; 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) → (5S,6S)-6-[(R)-1-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-tetrahydro-pyran-2-one (855127-41-2)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/ol050653q

upstream raw materials:

tert-butylchlorodiphenylsilane

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

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

(2R,3S,4S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-3-ol

Downstream raw materials:

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

[(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