(3S^*,4S^*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal

Base Information

• Chemical Name: (3S^*,4S^*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal
• CAS No.: 136850-71-0
• Molecular Formula: C₂₁H₃₆O₃Si
• Molecular Weight: 364.601
• Mol file: 136850-71-0.mol

Synonyms:(3S^*,4S^*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal

Chemical Property of (3S^*,4S^*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S^*,4S^*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal

There total 9 articles about (3S^*,4S^*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal 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: 91.0%

(3S*,4S*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctan-1-ol (136850-70-9) → (3S*,4S*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal (136850-71-0)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1248/cpb.39.1866

Reference yield:

methoxymethyl 5-crotyltetronate → (3S*,4S*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal (136850-71-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 75.9 percent / H₂ / 5percent rhodium on alumina / ethyl acetate / 4 h / 5320 Torr

2: 97.7 percent / lithium aluminium hydride / diethyl ether / 2 h / Ambient temperature

3: 78.3 percent / triethylamine / benzene / 6 h / Ambient temperature

4: NaH (60percent oil dispersion) / tetrahydrofuran / 6 h

5: tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

6: 95.1 percent / pyridine / tetrahydrofuran / 2 h / Ambient temperature

7: 81.9 percent / 10percent HCl / tetrahydrofuran / 2 h / Heating

8: 85.9 percent / imidazole / tetrahydrofuran / 6 h / Ambient temperature

9: 86.7 percent / 10percent aq. NaOH / methanol / 2 h / Ambient temperature

10: 91 percent / pyridinium chlorochromate (PCC), sodium acetate / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hydride; triethylamine; pyridinium chlorochromate; Rh/Al₂O₃; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; benzene;

DOI:10.1248/cpb.39.1866

Reference yield:

(3S*,4S*)-1-tert-butyldimethylsilyloxy-4-dihydroxy-3-methoxymethoxyoctane (136850-66-3) → (3S*,4S*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal (136850-71-0)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH (60percent oil dispersion) / tetrahydrofuran / 6 h

2: tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

3: 95.1 percent / pyridine / tetrahydrofuran / 2 h / Ambient temperature

4: 81.9 percent / 10percent HCl / tetrahydrofuran / 2 h / Heating

5: 85.9 percent / imidazole / tetrahydrofuran / 6 h / Ambient temperature

6: 86.7 percent / 10percent aq. NaOH / methanol / 2 h / Ambient temperature

7: 91 percent / pyridinium chlorochromate (PCC), sodium acetate / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; sodium hydroxide; tetrabutyl ammonium fluoride; sodium acetate; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1248/cpb.39.1866

upstream raw materials:

(3S^*,4S^*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctan-1-ol

(3S^*,4S^*)-1-tert-butyldimethylsilyloxy-4-dihydroxy-3-methoxymethoxyoctane

(3S^*,4S^*)-4-benzyloxy-3-methoxymethoxyoctan-1-ol

(3S^*,4S^*)-1-benzoyloxy-4-benzyloxy-3-hydroxyoctane

Downstream raw materials:

ethyl (5S^*,6S^*)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate

ethyl (5S^*,6S^*)-6-benzyloxy-5-hydroxy-3-oxodecanoate