3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid 1-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester

Base Information

• Chemical Name: 3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid 1-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester
• CAS No.: 869293-33-4
• Molecular Formula: C₂₉H₄₈O₆Si₂
• Molecular Weight: 548.868
• Mol file: 869293-33-4.mol

Synonyms:

Chemical Property of 3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid 1-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid 1-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester

There total 7 articles about 3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid 1-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-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:

(5R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-ol → 3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid 1-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester (869293-33-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 83 percent / DCC; DMAP

2.1: Grubbs catalyst II / CH₂Cl₂ / 12 h / 40 °C

3.1: 99 percent / HF / H₂O; acetonitrile

4.1: HCOOH; PPh₃; DEAD

4.2: 70 percent / HCl / dioxane

5.1: DCC; DMAP

6.1: DBU / CHCl₃

With dmap; formic acid; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; chloroform; water; acetonitrile; 4.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2005.08.164

Reference yield:

(R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one (869293-25-4) → 3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid 1-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester (869293-33-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 91 percent / NaBH₄; CeCl₃

2.1: 83 percent / DCC; DMAP

3.1: Grubbs catalyst II / CH₂Cl₂ / 12 h / 40 °C

4.1: 99 percent / HF / H₂O; acetonitrile

5.1: HCOOH; PPh₃; DEAD

5.2: 70 percent / HCl / dioxane

6.1: DCC; DMAP

7.1: DBU / CHCl₃

With dmap; sodium tetrahydroborate; formic acid; cerium(III) chloride; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; chloroform; water; acetonitrile; 1.1: Luche reaction / 5.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2005.08.164

Reference yield:

but-3-enoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-allyl ester → 3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid 1-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester (869293-33-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Grubbs catalyst II / CH₂Cl₂ / 12 h / 40 °C

2.1: 99 percent / HF / H₂O; acetonitrile

3.1: HCOOH; PPh₃; DEAD

3.2: 70 percent / HCl / dioxane

4.1: DCC; DMAP

5.1: DBU / CHCl₃

With dmap; formic acid; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; chloroform; water; acetonitrile; 3.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2005.08.164

upstream raw materials:

(R)-6-((S)-2-Hydroxy-propyl)-3,6-dihydro-pyran-2-one

(R)-6-((R)-2-Hydroxy-propyl)-3,6-dihydro-pyran-2-one

(R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one

(R)-6-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-3,6-dihydro-pyran-2-one