(3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one

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Chemical Name:(3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one
CAS No.:73407-87-1
Molecular Formula:C₂₆H₃₄O₅
Molecular Weight:426.553
Hs Code.:

Synonyms:(3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one

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Chemical Property of (3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one

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Technology Process of (3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one

There total 2 articles about (3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one 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: 87.0%

: 110-87-2
3,4-dihydro-2H-pyran

: 71686-37-8,73407-83-7,73407-85-9
(3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>-furan-2(3H)-one

: 73407-87-1
(3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo00151a016

Reference yield:

: 71686-37-8,73407-83-7,73407-85-9
(3aα,4α,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>-furan-2(3H)-one

: 73407-87-1
(3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: Standard Jones reagent / acetone / 0.33 h / -10 °C

2: sodium borohydride / ethanol / 0.25 h / 0 °C

3: 87 percent / p-TsOH / CH₂Cl₂ / 0.5 h / 0 °C

With sodium tetrahydroborate; Jones reagent; toluene-4-sulfonic acid; In ethanol; dichloromethane; acetone;
DOI:10.1021/jo00151a016

Reference yield:

: 73407-87-1
(3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one

: 3668-14-2,5988-99-8,6895-47-2,10180-86-6,70981-13-4,73465-50-6,95840-01-0
dl-Linifolin A

Guidance literature:: Multi-step reaction with 8 steps

2: 79 percent / p-TsOH / CH₂Cl₂ / 1.) 0 deg C, 2.) roomtemp., 3 h

4: 66 percent / pyridine / 1.) 0 deg C, 1 h, 2.) roomtemp., 30 min.

5: 1,5-Diazabicyclo<5.4.0>undec-5-ene / benzene / 0.5 h / Ambient temperature

6: 86 percent / acetic acid; H₂O / 1.5 h / 45 °C

7: 78 percent / Manganese dioxide / CH₂Cl₂; benzene / 0.5 h / Ambient temperature

8: 86 percent / 4-(dimethylamino)pyridine / pyridine / 3 h / Ambient temperature

With dmap; manganese(IV) oxide; toluene-4-sulfonic acid; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In pyridine; dichloromethane; water; acetic acid; benzene;
DOI:10.1021/jo00151a016