Furo[2,3-b]furan, hexahydro-2-(1-methylethyl)-, (2alpha,3aba,6aba)- (9CI)

Base Information

• Chemical Name: Furo[2,3-b]furan, hexahydro-2-(1-methylethyl)-, (2alpha,3aba,6aba)- (9CI)
• CAS No.: 117707-20-7
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.225
• Mol file: 117707-20-7.mol

Synonyms:Furo[2,3-b]furan,hexahydro-2-(1-methylethyl)-,(2alpha,3abta,6abta)-(9CI);Furo[2,3-b]furan, hexahydro-2-(1-methylethyl)-, (2alpha,3aba,6aba)- (9CI)

Chemical Property of Furo[2,3-b]furan, hexahydro-2-(1-methylethyl)-, (2alpha,3aba,6aba)- (9CI)

Chemical Property:

• PSA: 18.46000
• LogP: 1.79390

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Furo[2,3-b]furan, hexahydro-2-(1-methylethyl)-, (2alpha,3aba,6aba)- (9CI)

There total 10 articles about Furo[2,3-b]furan, hexahydro-2-(1-methylethyl)-, (2alpha,3aba,6aba)- (9CI) 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:

1-(2α-methoxyperhydrofur-3β-yl)-3-methylbutan-2-ol (117632-44-7) → 2β-isopropyl-2α,3,3aβ,4,5,6aβ-hexahydrofuro-<2,3b>-furan (117632-48-1,117707-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 20 h

2: 1.) potassium superoxide, 2.) sodium borohydride, 4N HCl / 1.) 18-crown-6 / 1.) DMSO, 1,2-dimethoxyethane, 1 h, below 35 deg C, 2.) DMSO, 1,2-dimethoxyethane, water, 15 min

With hydrogenchloride; dmap; potassium superoxide; sodium tetrahydroborate; triethylamine; 18-crown-6 ether; In dichloromethane;

DOI:10.1016/S0040-4020(01)81719-1

Reference yield:

1-(2α-methoxyperhydrofur-3β-yl)-3-methylbutan-2-one (117632-42-5,117632-50-5) → 2β-isopropyl-2α,3,3aβ,4,5,6aβ-hexahydrofuro-<2,3b>-furan (117632-48-1,117707-20-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / lithium-tri-tert-butoxyaluminohydride / tetrahydrofuran / 0.5 h / 0 °C

2: triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 20 h

3: 1.) potassium superoxide, 2.) sodium borohydride, 4N HCl / 1.) 18-crown-6 / 1.) DMSO, 1,2-dimethoxyethane, 1 h, below 35 deg C, 2.) DMSO, 1,2-dimethoxyethane, water, 15 min

With hydrogenchloride; dmap; potassium superoxide; sodium tetrahydroborate; lithium tri(t-butoxy)aluminum hydride; triethylamine; 18-crown-6 ether; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)81719-1

Reference yield:

2-methoxy-3-<(phenylthio)-methyl>-perhydrofuran (117632-30-1,117632-31-2) → 2β-isopropyl-2α,3,3aβ,4,5,6aβ-hexahydrofuro-<2,3b>-furan (117632-48-1,117707-20-7)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium bicarbonate, KHSO₅ / methanol; H₂O / 2 h

2: 1.) 15percent n-butyllithium / 1.) THF, hexane, - 78 deg C, 20 min, 2.) THF, hexane, - 78 deg C

3: 60 percent / disodium hydrogen phosphate, 5percent sodium amalgam / tetrahydrofuran; methanol / 1 h / Ambient temperature

4: 95 percent / lithium-tri-tert-butoxyaluminohydride / tetrahydrofuran / 0.5 h / 0 °C

5: triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 20 h

6: 1.) potassium superoxide, 2.) sodium borohydride, 4N HCl / 1.) 18-crown-6 / 1.) DMSO, 1,2-dimethoxyethane, 1 h, below 35 deg C, 2.) DMSO, 1,2-dimethoxyethane, water, 15 min

With hydrogenchloride; dmap; potassium superoxide; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; potassium peroxomonosulfate; n-butyllithium; lithium tri(t-butoxy)aluminum hydride; sodium hydrogencarbonate; triethylamine; 18-crown-6 ether; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/S0040-4020(01)81719-1

upstream raw materials:

1-(2α-methoxyperhydrofur-3β-yl)-3-methylbutan-2-one

2-methoxy-3-<(phenylthio)-methyl>-perhydrofuran

2α-methoxy-3β-<(phenylsulfonyl)-methyl>-perhydrofuran

1-Benzenesulfonyl-1-((2R,3R)-2-methoxy-tetrahydro-furan-3-yl)-3-methyl-butan-2-one

Refernces