(R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde

Base Information

• Chemical Name: (R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde
• CAS No.: 87118-61-4
• Molecular Formula: C₃₁H₄₈O₅Si₂
• Molecular Weight: 556.89
• Mol file: 87118-61-4.mol

Synonyms:

Chemical Property of (R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde

There total 10 articles about (R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-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:

(R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol → (R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde (87118-61-4)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; for 6h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(00)88094-6

Reference yield:

dimethyl 3-hydroxypentanedioate (7250-55-7) → (R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde (87118-61-4)

Guidance literature:

Multi-step reaction with 10 steps

1: chymotrypsin, H₂O

2: 95 percent / imidazole, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

3: 80 percent / KOH, H₂O / 2-methyl-propan-2-ol / 2 h / 50 °C

4: 1.) carbonyldiimidazole / 1.) THF, rt, 3 h, 2.) rt, 12 h

6: 80 percent / Hg(OOCCF₃)2 / tetrahydrofuran / 24 h / Ambient temperature

7: 65 percent / BH₃-THF / tetrahydrofuran / 4 h / Ambient temperature

8: 95 percent / imidazole, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

9: LiBH₄ / tetrahydrofuran / 6 h / Heating

10: PCC, NaOAc / CH₂Cl₂ / 6 h / Ambient temperature

With 1H-imidazole; dmap; potassium hydroxide; lithium borohydride; borane-THF; water; sodium acetate; mercury(II) trifluoroacetate; 1,1'-carbonyldiimidazole; pyridinium chlorochromate; chymotrypsin; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)88094-6

Reference yield:

(R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (87118-60-3) → (R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde (87118-61-4)

Guidance literature:

Multi-step reaction with 2 steps

1: LiBH₄ / tetrahydrofuran / 6 h / Heating

2: PCC, NaOAc / CH₂Cl₂ / 6 h / Ambient temperature

With lithium borohydride; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)88094-6

upstream raw materials:

dimethyl 3-hydroxypentanedioate

(R)-4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

(R)-3-hydroxypentanedioic acid monomethyl ester

(R)-((3-tert-butyldiphenylsillyl)oxy)pentanedioic acid monomethyl ester

Downstream raw materials:

(2E,4E)-(R)-8-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-7-(tert-butyl-diphenyl-silanyloxy)-octa-2,4-dienoic acid methyl ester

(E)-3-{3-[(R)-3-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolan-2-yl}-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-oxiranyl}-acrylic acid methyl ester