(R)-2-{(4R,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde

Base Information

• Chemical Name: (R)-2-{(4R,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde
• CAS No.: 129100-72-7
• Molecular Formula: C₂₉H₄₂O₄Si
• Molecular Weight: 482.736
• Mol file: 129100-72-7.mol

Synonyms:(R)-2-{(4R,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde

Chemical Property of (R)-2-{(4R,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-{(4R,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde

There total 31 articles about (R)-2-{(4R,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-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:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) → (R)-2-{(4R,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde (129100-72-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / 4A mol sieves / toluene / -78 °C

2: Et₃N / dimethylformamide

3: 1) ozone, 2)Me₂S / 1) MeOH, -78 deg C, 2) MeOH, -78 deg C to RT

4: 4A mol. sieves / toluene / -78 °C

5: 1N HCl / tetrahydrofuran

6: pyridinium tosylate

7: 1) ozone, 2) Me₂S / 1) MeOH, -78 deg C, 2) MeOH, -78 deg C to RT

With hydrogenchloride; dimethylsulfide; 4 A molecular sieve; pyridinium p-toluenesulfonate; ozone; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00237a082

Reference yield:

(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol (95514-04-8) → (R)-2-{(4R,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde (129100-72-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) a.) from -78 deg C to RT, b.) RT, 15 min

2: 4-A molecular sieves / toluene / 4 h / -78 °C

3: 98 percent / imidazole / dimethylformamide / 3 h / 0 °C

4: 1.) O₃, 2.) Me₂S / 1.) methanol, CH₂Cl₂, -78 deg C, 2.) RT, 2 h

5: 4-A molecular sieves / toluene / 11 h / -78 °C

6: 1 N HCl / tetrahydrofuran / 1 h / 45 °C

7: pyridinium p-toluenesulfonate (PPTS) / diethyl ether / 8 h / Ambient temperature

8: 1.) O₃, 2.) Me₂S / 1.) methanol, -78 deg C, 2.) RT, 2 h

With 1H-imidazole; hydrogenchloride; oxalyl dichloride; dimethylsulfide; 4 A molecular sieve; pyridinium p-toluenesulfonate; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene;

Reference yield:

C30H48O2Si2 → (R)-2-{(4R,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde (129100-72-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) ozone, 2)Me₂S / 1) MeOH, -78 deg C, 2) MeOH, -78 deg C to RT

2: 4A mol. sieves / toluene / -78 °C

3: 1N HCl / tetrahydrofuran

4: pyridinium tosylate

5: 1) ozone, 2) Me₂S / 1) MeOH, -78 deg C, 2) MeOH, -78 deg C to RT

With hydrogenchloride; dimethylsulfide; 4 A molecular sieve; pyridinium p-toluenesulfonate; ozone; In tetrahydrofuran; toluene;

DOI:10.1021/ja00237a082

upstream raw materials:

(4S,5R,6S)-4-{(1R)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-2,2,5-trimethyl-6-((1S)-1-methylprop-2-enyl)-1,3-dioxolane

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

(2S,3S,4R,5S,6S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4,6-trimethyl-oct-7-ene-3,5-diol

(3R,4R,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

Downstream raw materials:

(S)-2-{(4S,5S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propan-1-ol

6(S)-(1(S)-methyl-2-cyanoethyl)-4(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-2,2,5(S)-trimethyl-1,3-dioxane

[(2R,3R)-3-((S)-1-{(4R,5S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-oxiranyl]-methanol

[(2S,3S)-3-((S)-1-{(4R,5S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-oxiranyl]-methanol