(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
Hs Code.:

(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

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

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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

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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%

: 108-24-7
acetic anhydride

: 474526-57-3
(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

: 474526-59-5
(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

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:

: 80409-75-2,343865-40-7
cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole

: 474526-59-5
(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

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:

: 23780-59-8
4-hydroxybenzo[d][1,3]dioxole-5-carbaldehyde

: 474526-59-5
(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

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