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

Base Information

• Chemical Name: (3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione
• CAS No.: 73407-84-8
• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.419
• Mol file: 73407-84-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione 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:

(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 (71686-37-8,73407-83-7,73407-85-9) → (3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione (73407-84-8)

Guidance literature:

With Jones reagent; In acetone; at -10 ℃; for 0.333333h; Yield given;

DOI:10.1021/jo00151a016

Reference yield:

(3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione (73407-84-8) → (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 (71686-37-8,73407-83-7,73407-85-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.25h; Yield given;

DOI:10.1021/jo00151a016

Reference yield:

(3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione (73407-84-8) → dl-Linifolin A (3668-14-2,5988-99-8,6895-47-2,10180-86-6,70981-13-4,73465-50-6,95840-01-0)

Guidance literature:

Multi-step reaction with 10 steps

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

2: 87 percent / p-TsOH / CH₂Cl₂ / 0.5 h / 0 °C

4: 79 percent / p-TsOH / CH₂Cl₂ / 1.) 0 deg C, 2.) roomtemp., 3 h

6: 66 percent / pyridine / 1.) 0 deg C, 1 h, 2.) roomtemp., 30 min.

7: 1,5-Diazabicyclo<5.4.0>undec-5-ene / benzene / 0.5 h / Ambient temperature

8: 86 percent / acetic acid; H₂O / 1.5 h / 45 °C

9: 78 percent / Manganese dioxide / CH₂Cl₂; benzene / 0.5 h / Ambient temperature

10: 86 percent / 4-(dimethylamino)pyridine / pyridine / 3 h / Ambient temperature

With dmap; manganese(IV) oxide; sodium tetrahydroborate; toluene-4-sulfonic acid; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In pyridine; ethanol; dichloromethane; water; acetic acid; benzene;

DOI:10.1021/jo00151a016

upstream raw materials:

(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

Downstream raw materials:

(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

dl-Mexicanin I

dl-Linifolin A