(Z)-(3R,4S,7S,8R)-7-Acetoxy-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,8-dimethyl-non-5-enoic acid

Base Information

• Chemical Name: (Z)-(3R,4S,7S,8R)-7-Acetoxy-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,8-dimethyl-non-5-enoic acid
• CAS No.: 158497-96-2
• Molecular Formula: C₃₇H₄₈O₇Si
• Molecular Weight: 632.869

Synonyms:(Z)-(3R,4S,7S,8R)-7-Acetoxy-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,8-dimethyl-non-5-enoic acid

Chemical Property of (Z)-(3R,4S,7S,8R)-7-Acetoxy-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,8-dimethyl-non-5-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(3R,4S,7S,8R)-7-Acetoxy-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,8-dimethyl-non-5-enoic acid

There total 19 articles about (Z)-(3R,4S,7S,8R)-7-Acetoxy-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,8-dimethyl-non-5-enoic acid 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:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) → (Z)-(3R,4S,7S,8R)-7-Acetoxy-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,8-dimethyl-non-5-enoic acid (158497-96-2)

Guidance literature:

Multi-step reaction with 6 steps

1: CrCl₂, NiCl₂ / tetrahydrofuran / 4 h / Ambient temperature

2: H₂ / Pd(CaCO₃, Pb) / benzene / 760 Torr / Ambient temperature

3: DMAP, pyridine / Ambient temperature

4: PPTS / CH₂Cl₂; methanol / Ambient temperature

5: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

6: NaClO₂ / 2-methyl-propan-2-ol; various solvent(s) / 1 h / Ambient temperature

With pyridine; chromium dichloride; dmap; sodium chlorite; hydrogen; pyridinium p-toluenesulfonate; Dess-Martin periodane; nickel dichloride; palladium on calcium fluoride poisoned with lead; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; benzene;

DOI:10.1021/ja00091a082

Reference yield:

(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol (95514-04-8,129029-85-2,120346-83-0) → (Z)-(3R,4S,7S,8R)-7-Acetoxy-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,8-dimethyl-non-5-enoic acid (158497-96-2)

Guidance literature:

Multi-step reaction with 7 steps

1: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

2: CrCl₂, NiCl₂ / tetrahydrofuran / 4 h / Ambient temperature

3: H₂ / Pd(CaCO₃, Pb) / benzene / 760 Torr / Ambient temperature

4: DMAP, pyridine / Ambient temperature

5: PPTS / CH₂Cl₂; methanol / Ambient temperature

6: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

7: NaClO₂ / 2-methyl-propan-2-ol; various solvent(s) / 1 h / Ambient temperature

With pyridine; chromium dichloride; dmap; sodium chlorite; hydrogen; pyridinium p-toluenesulfonate; Dess-Martin periodane; nickel dichloride; palladium on calcium fluoride poisoned with lead; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; benzene;

DOI:10.1021/ja00091a082

Reference yield:

(R)-methyl 3-(tert-butyl(diphenyl)silyloxy)-2-methylpropanoate (95514-03-7) → (Z)-(3R,4S,7S,8R)-7-Acetoxy-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,8-dimethyl-non-5-enoic acid (158497-96-2)

Guidance literature:

Multi-step reaction with 8 steps

1: DIBAL / diethyl ether / -78 °C

2: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

3: CrCl₂, NiCl₂ / tetrahydrofuran / 4 h / Ambient temperature

4: H₂ / Pd(CaCO₃, Pb) / benzene / 760 Torr / Ambient temperature

5: DMAP, pyridine / Ambient temperature

6: PPTS / CH₂Cl₂; methanol / Ambient temperature

7: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

8: NaClO₂ / 2-methyl-propan-2-ol; various solvent(s) / 1 h / Ambient temperature

With pyridine; chromium dichloride; dmap; sodium chlorite; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; nickel dichloride; palladium on calcium fluoride poisoned with lead; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl alcohol; benzene;

DOI:10.1021/ja00091a082

upstream raw materials:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

(R)-methyl 3-(tert-butyl(diphenyl)silyloxy)-2-methylpropanoate

tert-butylchlorodiphenylsilane

Downstream raw materials:

(Z)-(3R,4S,7S,8R)-9-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-3-(4-methoxy-benzyloxy)-4,8-dimethyl-non-5-enoic acid

(S)-2-[(2S,5S,6R)-6-(4-Methoxy-benzyloxy)-5-methyl-8-oxo-oxocan-2-yl]-propionaldehyde

(4R,5S,8S)-8-((R)-2-Hydroxy-1-methyl-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-one

(4R,5S,8S)-8-((S)-2-{(2S,3R)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyl]-2-methyl-oxiranyl}-1-methyl-2-oxo-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-one

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