3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

Base Information

• Chemical Name: 3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione
• CAS No.: 170897-53-7
• Molecular Formula: C₂₈H₃₃NO₆Si
• Molecular Weight: 507.659
• Mol file: 170897-53-7.mol

Synonyms:

Chemical Property of 3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

There total 4 articles about 3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione 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:

β-1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-D-ribofuranose (29161-71-5) + 2-(triphenylphosphoranylidene)acetamide (38821-11-3) → 3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione (170897-53-7)

Guidance literature:

With ozone; Yield given. Multistep reaction;

DOI:10.1021/ja00300a036

Reference yield:

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (96690-02-7) → 3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione (170897-53-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / Cs₂CO₃ / CH₂Cl₂ / 5 h / 18 °C

2: 21 percent / CaH₂; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -50 °C

3: 77 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

4: 72 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 16 h / 18 °C

With calcium hydride; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; caesium carbonate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2003-41026

Reference yield:

5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate (478367-12-3) → 3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione (170897-53-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 21 percent / CaH₂; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -50 °C

2: 77 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

3: 72 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 16 h / 18 °C

With calcium hydride; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2003-41026

upstream raw materials:

β-1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-D-ribofuranose

2-(triphenylphosphoranylidene)acetamide

3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-furan-2,5-dione

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

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