(3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-4,8-dimethyl-3-oxonaphtho<1,8-bc>pyran p-toluenesulfonylhydrazone

Base Information

Chemical Name:(3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-4,8-dimethyl-3-oxonaphtho<1,8-bc>pyran p-toluenesulfonylhydrazone
CAS No.:101773-26-6
Molecular Formula:C₂₁H₂₈N₂O₃S
Molecular Weight:388.531
Hs Code.:

Synonyms:(3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-4,8-dimethyl-3-oxonaphtho<1,8-bc>pyran p-toluenesulfonylhydrazone

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Chemical Property of (3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-4,8-dimethyl-3-oxonaphtho<1,8-bc>pyran p-toluenesulfonylhydrazone

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Technology Process of (3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-4,8-dimethyl-3-oxonaphtho<1,8-bc>pyran p-toluenesulfonylhydrazone

There total 1 articles about (3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-4,8-dimethyl-3-oxonaphtho<1,8-bc>pyran p-toluenesulfonylhydrazone 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: 94.0%

: 1576-35-8
toluene-4-sulfonic acid hydrazide

: 99342-52-6
(3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-3-oxo-4,8-dimethylnaphtho<1,8-bc>pyran

: 101773-26-6
(3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-4,8-dimethyl-3-oxonaphtho<1,8-bc>pyran p-toluenesulfonylhydrazone

Guidance literature:: In methanol; for 18h; Ambient temperature;
DOI:10.1021/ja00275a053

Reference yield:

: 101773-26-6
(3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-4,8-dimethyl-3-oxonaphtho<1,8-bc>pyran p-toluenesulfonylhydrazone

: 101761-32-4
(1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-<(S)-(2-methylbutyryl)oxy>-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene

Guidance literature:: Multi-step reaction with 12 steps

1: 86 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / 2 °C

2: 99 percent / quinoline, hydrogen / Pd/BaSO₄ / 50 h

3: 92 percent / 4-(dimethylamino)pyridine / pyridine / 7 h / 60 °C / Heating

4: 95 percent / m-PCBA / CH₂Cl₂ / 1 h / 0 °C

5: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature

6: 85 percent / ozone, dimethyl sulfide / CH₂Cl₂ / 18 h / 40 °C / Heating

7: 91 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

8: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C

9: 85 percent / HCl / methanol / 15 h / 0 °C

10: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min

11: DMAP, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 0 °C

12: 96 percent / DMAP / pyridine / 3.33 h / 50 °C

With quinoline; hydrogenchloride; dmap; potassium hydroxide; n-butyllithium; dimethylsulfide; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; methyllithium; hydrogen; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/ja00275a053

Reference yield:

: 101773-26-6
(3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-4,8-dimethyl-3-oxonaphtho<1,8-bc>pyran p-toluenesulfonylhydrazone

: 101761-31-3
(1R,2R,4aS,6R,8R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene

Guidance literature:: Multi-step reaction with 11 steps

1: 86 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / 2 °C

2: 99 percent / quinoline, hydrogen / Pd/BaSO₄ / 50 h

3: 92 percent / 4-(dimethylamino)pyridine / pyridine / 7 h / 60 °C / Heating

4: 95 percent / m-PCBA / CH₂Cl₂ / 1 h / 0 °C

5: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature

6: 85 percent / ozone, dimethyl sulfide / CH₂Cl₂ / 18 h / 40 °C / Heating

7: 91 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

8: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C

9: 85 percent / HCl / methanol / 15 h / 0 °C

10: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min

11: DMAP, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 0 °C

With quinoline; hydrogenchloride; dmap; potassium hydroxide; n-butyllithium; dimethylsulfide; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; methyllithium; hydrogen; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/ja00275a053