(3aα,3bβ,6aβ,7aα)-(+/-)-hexahydro-6-hydroxy-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-one

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Chemical Name:(3aα,3bβ,6aβ,7aα)-(+/-)-hexahydro-6-hydroxy-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-one
CAS No.:107353-12-8
Molecular Formula:C₁₅H₁₆O₅
Molecular Weight:276.289
Hs Code.:

Synonyms:(3aα,3bβ,6aβ,7aα)-(+/-)-hexahydro-6-hydroxy-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-one

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Chemical Property of (3aα,3bβ,6aβ,7aα)-(+/-)-hexahydro-6-hydroxy-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-one

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Technology Process of (3aα,3bβ,6aβ,7aα)-(+/-)-hexahydro-6-hydroxy-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-one

There total 8 articles about (3aα,3bβ,6aβ,7aα)-(+/-)-hexahydro-6-hydroxy-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-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: 57.6%

: 107353-11-7,107438-25-5
(3aα,3bβ,6aβ,7aα)-hexahydro-6-(2-hydroxyethoxy)-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-one

: 107353-12-8
(3aα,3bβ,6aβ,7aα)-(+/-)-hexahydro-6-hydroxy-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-one

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; at 0 - 20 ℃; for 3.5h;
DOI:10.1021/jo00383a002

Reference yield:

: 107353-02-6
cis-(+/-)-5-(1,3-dioxolan-2-yl)dihydro-4-<(phenylmethoxy)methyl>-2(3H)-furanone

: 107353-12-8
(3aα,3bβ,6aβ,7aα)-(+/-)-hexahydro-6-hydroxy-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) lithium diisipropylamide / 1.) THF, -78 deg C, 1.25 h, 2.) THF, HMPA, -78 deg C, 3.5 h

2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 0.75 h, 2.) THF, HMPA, -78 deg C, 3.5 h

3: 90.3 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

4: 1.) diisobutylaluminium hydride, 2.) p-toluenosulfonic acid / 1.) toluene, -78 deg C, 4.5 h, 2.) toluene, 80 deg C, 2 min

5: 73.2 percent / H₂ / 10percent Pd/C / ethanol / 20 h / 2585.7 Torr / Ambient temperature

6: p-toluenesulfonic acid / toluene / 0.75 h / 60 °C

7: 57.6 percent / ag. HCl / tetrahydrofuran / 3.5 h / 0 - 20 °C

With hydrogenchloride; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene;
DOI:10.1021/jo00383a002

Reference yield:

: cis-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-furancarboxylic acid methyl ester

: 107353-12-8
(3aα,3bβ,6aβ,7aα)-(+/-)-hexahydro-6-hydroxy-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-one

Guidance literature:: Multi-step reaction with 8 steps

1: 84.1 percent / LiCl / dimethylsulfoxide; H₂O / 25 h / 110 °C

2: 1.) lithium diisipropylamide / 1.) THF, -78 deg C, 1.25 h, 2.) THF, HMPA, -78 deg C, 3.5 h

3: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 0.75 h, 2.) THF, HMPA, -78 deg C, 3.5 h

4: 90.3 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

5: 1.) diisobutylaluminium hydride, 2.) p-toluenosulfonic acid / 1.) toluene, -78 deg C, 4.5 h, 2.) toluene, 80 deg C, 2 min

6: 73.2 percent / H₂ / 10percent Pd/C / ethanol / 20 h / 2585.7 Torr / Ambient temperature

7: p-toluenesulfonic acid / toluene / 0.75 h / 60 °C

8: 57.6 percent / ag. HCl / tetrahydrofuran / 3.5 h / 0 - 20 °C

With hydrogenchloride; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; lithium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1021/jo00383a002