(E)-(10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester
• CAS No.: 207572-41-6
• Molecular Formula: C₃₀H₅₀O₅Si
• Molecular Weight: 518.809

Synonyms:(E)-(10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

Chemical Property of (E)-(10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

There total 9 articles about (E)-(10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester 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:

t-butyldimethylsiyl triflate (69739-34-0) → (E)-(10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester (207572-41-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 95 percent / Mg / methanol / Ambient temperature

3: DIBAL-H / CH₂Cl₂ / -78 °C

4: 78 percent / Mg / diethyl ether / 0 °C

5: 76 percent / PCC / CH₂Cl₂ / 0 °C

6: 1.) O₃, Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) C₆H₆, r.t.

With 2,6-dimethylpyridine; diisobutylaluminium hydride; ozone; magnesium; triphenylphosphine; pyridinium chlorochromate; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(98)00320-7

Reference yield:

((2S,3R)-3-((R)-1-(benzyloxy)propan-2-yl)oxiran-2-yl)methanol (125873-80-5) → (E)-(10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester (207572-41-6)

Guidance literature:

Multi-step reaction with 9 steps

1: CrO₃, py / CH₂Cl₂ / 0 °C

2: benzene / Ambient temperature

3: 85 percent / H₂O; CH₂Cl₂ / -30 °C

4: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 95 percent / Mg / methanol / Ambient temperature

6: DIBAL-H / CH₂Cl₂ / -78 °C

7: 78 percent / Mg / diethyl ether / 0 °C

8: 76 percent / PCC / CH₂Cl₂ / 0 °C

9: 1.) O₃, Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) C₆H₆, r.t.

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; diisobutylaluminium hydride; ozone; magnesium; triphenylphosphine; pyridinium chlorochromate; In methanol; diethyl ether; dichloromethane; water; benzene;

DOI:10.1016/S0040-4039(98)00320-7

Reference yield:

(E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-enoic acid ethyl ester (179944-92-4) → (E)-(10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester (207572-41-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / Mg / methanol / Ambient temperature

2: DIBAL-H / CH₂Cl₂ / -78 °C

3: 78 percent / Mg / diethyl ether / 0 °C

4: 76 percent / PCC / CH₂Cl₂ / 0 °C

5: 1.) O₃, Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) C₆H₆, r.t.

With diisobutylaluminium hydride; ozone; magnesium; triphenylphosphine; pyridinium chlorochromate; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(98)00320-7

upstream raw materials:

ethyl (triphenylphosphoranylidene)acetate

(9R,10S,11R)-12-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-9,11-dimethyl-dodec-1-en-6-one

t-butyldimethylsiyl triflate

((2S,3R)-3-((R)-1-(benzyloxy)propan-2-yl)oxiran-2-yl)methanol

Downstream raw materials:

{(2S,6S,8S,9R)-8-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-acetic acid methyl ester

[(2S,6S,8S,9R)-8-((R)-2-Benzyloxy-1-methyl-ethyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid methyl ester

(βR,2S,3R,6S,8S)-2-[α-(tert-butyldiphenylsilyloxy)ethyl]-β,3-dimethyl-1,7-dioxaspiro[5.5]undecane-8-ethanol

(E)-(10R,11S,12R)-13-Benzyloxy-11-hydroxy-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

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