(-)-4β-<(benzyloxy)methyl>-2α-<(tert-butyldimethylsilyl)oxy>-1α-cyclohexanecarboxaldehyde

Base Information

• Chemical Name: (-)-4β-<(benzyloxy)methyl>-2α-<(tert-butyldimethylsilyl)oxy>-1α-cyclohexanecarboxaldehyde
• CAS No.: 89690-21-1
• Molecular Formula: C₂₁H₃₄O₃Si
• Molecular Weight: 362.585
• Mol file: 89690-21-1.mol

Synonyms:(-)-4β-<(benzyloxy)methyl>-2α-<(tert-butyldimethylsilyl)oxy>-1α-cyclohexanecarboxaldehyde

Chemical Property of (-)-4β-<(benzyloxy)methyl>-2α-<(tert-butyldimethylsilyl)oxy>-1α-cyclohexanecarboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-4β-<(benzyloxy)methyl>-2α-<(tert-butyldimethylsilyl)oxy>-1α-cyclohexanecarboxaldehyde

There total 1 articles about (-)-4β-<(benzyloxy)methyl>-2α-<(tert-butyldimethylsilyl)oxy>-1α-cyclohexanecarboxaldehyde 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,4S)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-methanol → (1R,2R,4S)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarbaldehyde + (-)-4β-<(benzyloxy)methyl>-2α-<(tert-butyldimethylsilyl)oxy>-1α-cyclohexanecarboxaldehyde (89690-21-1)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/ja00322a035

Reference yield:

2-<1-(tert-butyldiphenylsiloxy)-2(R)-methyl-3(S)-((β-methoxyethoxy)methoxy)butyl>-1,3-dithiane + (-)-4β-<(benzyloxy)methyl>-2α-<(tert-butyldimethylsilyl)oxy>-1α-cyclohexanecarboxaldehyde (89690-21-1) → (S)-4-<(benzyloxy)methyl>-1-cyclohexenecarboxaldehyde + (R)-[(1R,2R,4S)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-{2-[(2S,3R)-4-(tert-butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl]-[1,3]dithian-2-yl}-methanol + (S)-[(1R,2R,4S)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-{2-[(2S,3R)-4-(tert-butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl]-[1,3]dithian-2-yl}-methanol

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; Yield given;

DOI:10.1021/ja00322a035

Reference yield:

(-)-4β-<(benzyloxy)methyl>-2α-<(tert-butyldimethylsilyl)oxy>-1α-cyclohexanecarboxaldehyde (89690-21-1) → (1R,2S,5S)-5-Benzyloxymethyl-2-((R)-hydroxy-{2-[(2S,3R)-4-hydroxy-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl]-[1,3]dithian-2-yl}-methyl)-cyclohexanol

Guidance literature:

Multi-step reaction with 2 steps

1: hexamethylphosphoramide, t-BuLi / tetrahydrofuran / -78 °C

2: 50.6 percent / n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; tert.-butyl lithium; In tetrahydrofuran;

DOI:10.1021/ja00322a035