(3α,4β,5β)-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-(phenylmethyl)-2(3H)-furanacetic acid

Base Information

Chemical Name:(3α,4β,5β)-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-(phenylmethyl)-2(3H)-furanacetic acid
CAS No.:107353-05-9
Molecular Formula:C₂₄H₂₆O₇
Molecular Weight:426.466
Hs Code.:

Synonyms:(3α,4β,5β)-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-(phenylmethyl)-2(3H)-furanacetic acid

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Chemical Property of (3α,4β,5β)-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-(phenylmethyl)-2(3H)-furanacetic acid

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Technology Process of (3α,4β,5β)-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-(phenylmethyl)-2(3H)-furanacetic acid

There total 5 articles about (3α,4β,5β)-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-(phenylmethyl)-2(3H)-furanacetic acid 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: 90.3%

: 107353-04-8
(3α,4β,5β)-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-(phenylmethyl)-2(3H)-furanacetic acid 1,1-dimethylethyl ester

: 107353-05-9
(3α,4β,5β)-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-(phenylmethyl)-2(3H)-furanacetic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 3h; Ambient temperature;
DOI:10.1021/jo00383a002

Reference yield:

: 99883-88-2
2-(3-Benzyloxymethyl-oxiranyl)-[1,3]dioxolane

: 107353-05-9
(3α,4β,5β)-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-(phenylmethyl)-2(3H)-furanacetic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 54.8 percent / methanol / 48 h / Heating

2: 84.1 percent / LiCl / dimethylsulfoxide; H₂O / 25 h / 110 °C

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

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

5: 90.3 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

With trifluoroacetic acid; lithium chloride; lithium diisopropyl amide; In methanol; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1021/jo00383a002

Reference yield:

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

: 107353-05-9
(3α,4β,5β)-(+/-)-5-(1,3-dioxolan-2-yl)tetrahydro-2-oxo-4-<(phenylmethoxy)methyl>-3-(phenylmethyl)-2(3H)-furanacetic acid

Guidance literature:: Multi-step reaction with 3 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

With trifluoroacetic acid; lithium diisopropyl amide; In dichloromethane;
DOI:10.1021/jo00383a002