(R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde

Base Information

• Chemical Name: (R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde
• CAS No.: 864382-64-9
• Molecular Formula: C₂₃H₃₀O₂Si
• Molecular Weight: 366.576
• Mol file: 864382-64-9.mol

Synonyms:(R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde

Chemical Property of (R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde

There total 5 articles about (R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde 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:

(2R)-2-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-1-ol (460997-43-7) → (R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde (864382-64-9)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 20 ℃;

DOI:10.1002/1521-3773(20020617)41:12<2144::AID-ANIE2144>3.0.CO;2-E

Reference yield:

(1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-isopropenylcyclopropane (334705-97-4) → (R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde (864382-64-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BH₃*THF / tetrahydrofuran / 2.5 h / -30 - 20 °C

1.2: 91 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 20 °C

2.1: PCC / CH₂Cl₂ / 1.5 h / 20 °C

With borane-THF; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0496042

Reference yield:

allyl diazoacetate (4606-10-4) → (R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde (864382-64-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 91 percent / Rh₂((5R)-MEPY)4 / CH₂Cl₂ / 30 h / Heating

2.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

2.2: 90 percent / imidazole / diethyl ether; tetrahydrofuran; dimethylformamide / 20 °C

3.1: 85 percent / Et₃N; DMAP; MsCl / CH₂Cl₂ / 5 h / 0 °C

4.1: BH₃*THF / tetrahydrofuran / 2.5 h / -30 - 20 °C

4.2: 91 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 20 °C

5.1: PCC / CH₂Cl₂ / 1.5 h / 20 °C

With dmap; borane-THF; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; Doyle dirhodium catalyst; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo0496042

upstream raw materials:

(2R)-2-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-1-ol

(1S,5R)-3-oxabicyclo[3.1.0]hexan-2-one

allyl diazoacetate

(1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-isopropenylcyclopropane

Downstream raw materials:

(1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate

ethyl (4S)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pentanoate

(1S,3S,4S,7S)-4-hydroxy-7-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-1,3-dimethyl-2-oxooctyl benzoate

(4S)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pentanal