(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine

Base Information

• Chemical Name: (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine
• CAS No.: 474526-59-5
• Molecular Formula: C₃₆H₄₉N₃O₁₃SSi
• Molecular Weight: 791.949
• Mol file: 474526-59-5.mol

Synonyms:(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine

Chemical Property of (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine

There total 10 articles about (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine 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%

acetic anhydride (108-24-7) + (1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol (474526-57-3) → (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine (474526-59-5)

Guidance literature:

(1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol; With tin(IV) chloride; In dichloromethane; at 25 ℃; for 0.333333h;

acetic anhydride; With pyridine; dmap; potassium carbonate; In dichloromethane; at 25 ℃; for 6h; Further stages.;

DOI:10.1021/jo020155k

Reference yield:

cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole (80409-75-2,343865-40-7) → (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine (474526-59-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: chiral chloronitroso synthon / CH₂Cl₂ / 12 h / 0 °C

1.2: 85 percent / Al-Hg / acetonitrile; H₂O / 1.5 h / 20 °C

2.1: Et₃N / acetonitrile / 8 h / 25 °C

3.1: 3.78 g / DBU / acetonitrile / 9 h / 25 °C

4.1: NBS / H₂O; acetone / 10 h / 20 °C

4.2: 88 percent / K₂CO₃ / acetonitrile / 4 h / 60 °C

5.1: SnCl₄ / CH₂Cl₂ / 0.33 h / 25 °C

5.2: 98 percent / DMAP; K₂CO₃; pyridine / CH₂Cl₂ / 6 h / 25 °C

With N-Bromosuccinimide; chiral chloronitroso synthon; tin(IV) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/jo020155k

Reference yield:

4-hydroxybenzo[d][1,3]dioxole-5-carbaldehyde (23780-59-8) → (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine (474526-59-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: K₂CO₃ / acetonitrile / 2 h / 85 °C

2.1: NaBH₄ / methanol / 0 - 25 °C

3.1: HBr / CH₂Cl₂; H₂O / 25 °C

4.1: NBS / H₂O; acetone / 10 h / 20 °C

4.2: 88 percent / K₂CO₃ / acetonitrile / 4 h / 60 °C

5.1: SnCl₄ / CH₂Cl₂ / 0.33 h / 25 °C

5.2: 98 percent / DMAP; K₂CO₃; pyridine / CH₂Cl₂ / 6 h / 25 °C

With sodium tetrahydroborate; N-Bromosuccinimide; hydrogen bromide; tin(IV) chloride; potassium carbonate; In methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/jo020155k

upstream raw materials:

acetic anhydride

(1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol

cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole

4-hydroxybenzo[d][1,3]dioxole-5-carbaldehyde

Downstream raw materials:

narciclasine