(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine

Base Information

Chemical Name:(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine
CAS No.:475275-64-0
Molecular Formula:C₃₂H₄₃NO₉SSi
Molecular Weight:645.846
Hs Code.:

(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine

Synonyms:(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine

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Chemical Property of (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine

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Technology Process of (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine

There total 6 articles about (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine 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: 93.0%

: 108-24-7
acetic anhydride

: 393165-27-0
(1R,2R,3S,4S,5S,6R)-4,5-(isopropylidenedioxy)-3-[(tert-butyldimethylsilyl)oxy]-6-N-(3',4'-methylenedioxybenzyl)-N-(4'-methylphenylsulfonyl)-7-oxabicyclo[4.1.0]heptane

: 475275-64-0
(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine

Guidance literature:: (1R,2R,3S,4S,5S,6R)-4,5-(isopropylidenedioxy)-3-[(tert-butyldimethylsilyl)oxy]-6-N-(3',4'-methylenedioxybenzyl)-N-(4'-methylphenylsulfonyl)-7-oxabicyclo[4.1.0]heptane; With tin(IV) chloride; In dichloromethane; at 25 ℃; for 0.333333h;

acetic anhydride; With dmap; potassium carbonate; In pyridine; dichloromethane; for 6h;
DOI:10.1016/S0040-4020(02)00736-6

Reference yield:

: 2606-51-1
3,4-Methylenedioxybenzyl bromide

: 475275-64-0
(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine

Guidance literature:: Multi-step reaction with 2 steps

1.1: NBS / acetone; H₂O / 10 h / 25 °C

1.2: Bu₄NHSO₄; aq. NaOH / CH₂Cl₂ / 8 h / 20 °C

1.3: 91 percent / CH₂Cl₂ / 7 h / 20 °C

2.1: SnCl₄ / CH₂Cl₂ / 0.33 h / 25 °C

2.2: 93 percent / K₂CO₃; DMAP / pyridine; CH₂Cl₂ / 6 h

With N-Bromosuccinimide; tin(IV) chloride; In dichloromethane; water; acetone;
DOI:10.1016/S0040-4020(02)00736-6

Reference yield:

: 137775-67-8
(1S,4R,5S,6R)-(-)-4-Amino-5,6-O-isopropylidenedioxycyclohex-2-en-1-ol

: 475275-64-0
(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine

Guidance literature:: Multi-step reaction with 3 steps

1.1: NEt₃ / acetonitrile / 8 h / 25 °C

1.2: 78 percent / acetonitrile / 9 h / 25 °C

2.1: NBS / acetone; H₂O / 10 h / 25 °C

2.2: Bu₄NHSO₄; aq. NaOH / CH₂Cl₂ / 8 h / 20 °C

2.3: 91 percent / CH₂Cl₂ / 7 h / 20 °C

3.1: SnCl₄ / CH₂Cl₂ / 0.33 h / 25 °C

3.2: 93 percent / K₂CO₃; DMAP / pyridine; CH₂Cl₂ / 6 h

With N-Bromosuccinimide; tin(IV) chloride; triethylamine; In dichloromethane; water; acetone; acetonitrile;
DOI:10.1016/S0040-4020(02)00736-6