5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-D-erythro-pentonic-γ-lactone

Base Information

• Chemical Name: 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-D-erythro-pentonic-γ-lactone
• CAS No.: 147200-09-7
• Molecular Formula: C₂₂H₂₈O₃Si
• Molecular Weight: 368.548
• Mol file: 147200-09-7.mol

Synonyms:5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-D-erythro-pentonic-γ-lactone

Chemical Property of 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-D-erythro-pentonic-γ-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-D-erythro-pentonic-γ-lactone

There total 15 articles about 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-D-erythro-pentonic-γ-lactone 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: 98.0%

5S-5-(t-butyldiphenylsiloxymethyl)-3-methyl-2(5H)-furanone (147093-37-6) → 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-D-erythro-pentonic-γ-lactone (147200-09-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 5h; under 7500.6 Torr; Ambient temperature;

DOI:10.1016/S0957-4166(00)86022-X

Reference yield: 58.7%

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one (102717-29-3) + methyl iodide (74-88-4) → (2R,4S)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-methyl-4-butanolide (103233-24-5) + 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-D-erythro-pentonic-γ-lactone (147200-09-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1080/07328319608002379

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-D-erythro-pentonic-γ-lactone (147200-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 58.7 percent / LDA / tetrahydrofuran / 2 h / -78 °C

With 1H-imidazole; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1080/07328319608002379

upstream raw materials:

S-γ-tert-butyldiphenylsilyloxymethyl-γ-butyrolactone

methyl iodide

5S-5-(t-butyldiphenylsiloxymethyl)-3-methyl-2(5H)-furanone

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

Downstream raw materials:

tert-butyl({(2S,4S,5R)-4-methyl-5-[4-(trifluoromethyl)phenyl]tetrahydrofuran-2-yl}methoxy)diphenylsilane

(3S,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-3-methyl-2-(4-(trifluoromethyl)phenyl)tetrahydrofuran-2-ol

N⁴-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-β-D-erythro-pentofuranosyl>uracil

N⁴-benzoyl-1-<(5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-α-D-erythro-pentofuranosyl>uracil