(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-butyraldehyde

Base Information

• Chemical Name: (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-butyraldehyde
• CAS No.: 198192-49-3
• Molecular Formula: C₂₇H₃₈O₄Si
• Molecular Weight: 454.682
• Mol file: 198192-49-3.mol

Synonyms:(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-butyraldehyde

Chemical Property of (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-butyraldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-butyraldehyde

There total 4 articles about (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-butyraldehyde 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: 100.0%

tert-Butyl-[(R)-1-((S)-2,2-diethyl-[1,3]dioxolan-4-ylmethyl)-but-3-enyloxy]-diphenyl-silane (198193-01-0) → (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-butyraldehyde (198192-49-3)

Guidance literature:

With ozone; In dichloromethane; at -78 ℃;

DOI:10.1021/ja972497r

Reference yield:

(S)-(2,2-diethyl-[1,3]dioxan-4-yl)acetaldehyde (127793-59-3) → (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-butyraldehyde (198192-49-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / (+)-B-methoxy(diisopinocampheyl)borane / toluene / 1 h / -78 °C

2: 100 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / Ambient temperature

3: 100 percent / ozone / CH₂Cl₂ / -78 °C

With 1H-imidazole; dmap; ozone; (+)-B-methoxydiisocamphenylborane; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja972497r

Reference yield:

(4S)-4-(2-hydroxyethyl)-2,2-diethyl-1,3-dioxolane (90941-88-1) → (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-butyraldehyde (198192-49-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 2 h / 0 - 20 °C

2: 75 percent / (+)-B-methoxy(diisopinocampheyl)borane / toluene / 1 h / -78 °C

3: 100 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / Ambient temperature

4: 100 percent / ozone / CH₂Cl₂ / -78 °C

With 1H-imidazole; dmap; sodium acetate; ozone; (+)-B-methoxydiisocamphenylborane; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja972497r

upstream raw materials:

tert-Butyl-[(R)-1-((S)-2,2-diethyl-[1,3]dioxolan-4-ylmethyl)-but-3-enyloxy]-diphenyl-silane

(4S)-4-(2-hydroxyethyl)-2,2-diethyl-1,3-dioxolane

(S)-(2,2-diethyl-[1,3]dioxan-4-yl)acetaldehyde

(2R)-1-[(4S)-2,2-diethyl-[1,3]dioxolan-4-yl]-pent-4-en-2-ol

Downstream raw materials:

2β-methoxy-4β-(diphenyl t-butylsiloxy)-6α-hydroxymethyl-tetrahydro-2H-pyran

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (E)-(1S,2S)-4-[(2S,4S,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-ethoxycarbonylmethyl-6-methoxy-tetrahydro-pyran-2-yl]-1-(1-ethylsulfanylcarbonyl-1-methyl-ethyl)-2-methyl-pent-3-enyl ester

(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (E)-(1S,2S)-4-[(2S,4S,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-ethoxycarbonylmethyl-6-methoxy-tetrahydro-pyran-2-yl]-1-(1-ethylsulfanylcarbonyl-1-methyl-ethyl)-2-methyl-pent-3-enyl ester

[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester