(E)-(2S,6R,7R,8R)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-triisopropylsilanyloxy-dec-3-en-5-one

Base Information

• Chemical Name: (E)-(2S,6R,7R,8R)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-triisopropylsilanyloxy-dec-3-en-5-one
• CAS No.: 152192-55-7
• Molecular Formula: C₄₄H₈₀O₆Si₂
• Molecular Weight: 761.287
• Mol file: 152192-55-7.mol

Synonyms:(E)-(2S,6R,7R,8R)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-triisopropylsilanyloxy-dec-3-en-5-one

Chemical Property of (E)-(2S,6R,7R,8R)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-triisopropylsilanyloxy-dec-3-en-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,6R,7R,8R)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-triisopropylsilanyloxy-dec-3-en-5-one

There total 14 articles about (E)-(2S,6R,7R,8R)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-triisopropylsilanyloxy-dec-3-en-5-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: 95.0%

((3R,4R,5R)-4-Methoxy-3,5-dimethyl-2-oxo-7-triisopropylsilanyloxy-heptyl)-phosphonic acid dimethyl ester (152192-48-8) + (R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde (152192-49-9) → (E)-(2S,6R,7R,8R)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-triisopropylsilanyloxy-dec-3-en-5-one (152192-55-7)

Guidance literature:

With barium dihydroxide; In tetrahydrofuran; water; for 3.5h;

DOI:10.1016/S0040-4039(00)73994-3

Reference yield:

(2S,3R,4R)-1-benzyloxy-2,4-dimethylhex-5-en-3-ol (106357-29-3) → (E)-(2S,6R,7R,8R)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-triisopropylsilanyloxy-dec-3-en-5-one (152192-55-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaH / 1.) THF, room temperature, 15 min, 2.) room temperature, 17 h.

2: 1.) 9-BBN, 2.) H₂O₂, NaOH / 1.) THF, room temperature, 5 h, 2.) THF, EtOH, H₂O, room temperature, 3 h.

3: 99 percent / imidazole / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 91 percent / H₂ / Pd-C / ethanol / 6 h / Ambient temperature

5: 0.55 g / Dess-Martin periodinate / CH₂Cl₂ / 6 h / Ambient temperature

6: 1.) nBuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, -78 deg C, 15 min.

7: 82 percent / pyridinium dichromate, moleculoar sieves 3 Angstroem / dimethylformamide / 1 h / 30 °C

8: 1.) Ba(OH)2*8H₂O / 1.) THF, room temperature, 30 min, 2.) THF, H₂O, room temperature, 6.5 h.

With 1H-imidazole; barium dihydroxide; sodium hydroxide; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 3 A molecular sieve; hydrogen; dihydrogen peroxide; sodium hydride; Dess-Martin periodane; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)83050-0

Reference yield:

((2S,3R,4R)-3-Methoxy-2,4-dimethyl-hex-5-enyloxymethyl)-benzene (176444-17-0) → (E)-(2S,6R,7R,8R)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-triisopropylsilanyloxy-dec-3-en-5-one (152192-55-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 9-BBN, 2.) H₂O₂, NaOH / 1.) THF, room temperature, 5 h, 2.) THF, EtOH, H₂O, room temperature, 3 h.

2: 99 percent / imidazole / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 91 percent / H₂ / Pd-C / ethanol / 6 h / Ambient temperature

4: 0.55 g / Dess-Martin periodinate / CH₂Cl₂ / 6 h / Ambient temperature

5: 1.) nBuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, -78 deg C, 15 min.

6: 82 percent / pyridinium dichromate, moleculoar sieves 3 Angstroem / dimethylformamide / 1 h / 30 °C

7: 1.) Ba(OH)2*8H₂O / 1.) THF, room temperature, 30 min, 2.) THF, H₂O, room temperature, 6.5 h.

With 1H-imidazole; barium dihydroxide; sodium hydroxide; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 3 A molecular sieve; hydrogen; dihydrogen peroxide; Dess-Martin periodane; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)83050-0

upstream raw materials:

((3R,4R,5R)-4-Methoxy-3,5-dimethyl-2-oxo-7-triisopropylsilanyloxy-heptyl)-phosphonic acid dimethyl ester

(R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde

(2S,3R,4R)-1-benzyloxy-2,4-dimethylhex-5-en-3-ol

(S)-1-benzyloxy-2-methylpentan-3-one