5-(tert-Butyl-diphenyl-silanyloxy)-1-[(3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentan-2-one

Base Information

• Chemical Name: 5-(tert-Butyl-diphenyl-silanyloxy)-1-[(3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentan-2-one
• CAS No.: 143135-50-6
• Molecular Formula: C₃₀H₄₂O₇Si
• Molecular Weight: 542.745

Synonyms:

Chemical Property of 5-(tert-Butyl-diphenyl-silanyloxy)-1-[(3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(tert-Butyl-diphenyl-silanyloxy)-1-[(3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentan-2-one

There total 6 articles about 5-(tert-Butyl-diphenyl-silanyloxy)-1-[(3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentan-2-one 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: 56.0%

3-Deoxy-1,2:5,6-di-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuranose (143135-28-8) → (3aR,4aS,5R,8aR,8bR)-5-Hydroxymethyl-7-(3-hydroxy-propyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyran-7-ol + 5-(tert-Butyl-diphenyl-silanyloxy)-1-[(3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentan-2-one (143135-50-6)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; for 15h;

DOI:10.1016/S0040-4020(01)80440-3

Reference yield:

1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside (18427-19-5) → 5-(tert-Butyl-diphenyl-silanyloxy)-1-[(3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentan-2-one (143135-50-6)

Guidance literature:

Multi-step reaction with 6 steps

1: PCC, molecular sieves 4A / CH₂Cl₂ / 0.75 h

2: 87 percent / tetrahydrofuran / 0.75 h / Ambient temperature

3: 1) BH₃*THF, 2) 35percent aq. H₂O₂, 3M aq. NaOH / 1) THF, 0 deg C, 3h, 2) water, 30 min

4: imidazole / dimethylformamide / 3 h

5: 98 percent / PCC, molecular sieve 4A / CH₂Cl₂ / 1 h

6: 56 percent / AcOH / tetrahydrofuran; H₂O / 15 h

With 1H-imidazole; sodium hydroxide; borane-THF; 4 A molecular sieve; dihydrogen peroxide; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80440-3

Reference yield:

5-[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentane-1,4-diol (143135-48-2,143135-49-3) → 5-(tert-Butyl-diphenyl-silanyloxy)-1-[(3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentan-2-one (143135-50-6)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 3 h

2: 98 percent / PCC, molecular sieve 4A / CH₂Cl₂ / 1 h

3: 56 percent / AcOH / tetrahydrofuran; H₂O / 15 h

With 1H-imidazole; 4 A molecular sieve; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80440-3

upstream raw materials:

3-Deoxy-1,2:5,6-di-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuranose

1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside

5-[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentane-1,4-diol

[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetaldehyde

Downstream raw materials:

3-Deoxy-1,2-O-isopropylidene-3-C-<<2-oxo-5-(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-1,4-dialdo-ribofuranose

(1R,3S,8R,9R)-11,11-Dimethyl-5-<2-(tert-butyldiphenylsiloxy)ethyl>-2,10,12-trioxatricyclo<7.3.0.0^3,8>dodec-4-en-6-one

(1R,3R,4R,8R,9R)-4,11,11-Trimethyl-5-<2-(tert-butyldiphenylsilyl)oxyethyl>-2,10,12-trioxatricyclo<7.3.0.0^3,8>dodecan-6-one

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