(5R)-5-[(1S)-3-(benzyloxy)-1-hydroxypropyl]-3,3-dimethylfuran-2,4(3H,5H)-dione

Base Information

Chemical Name:(5R)-5-[(1S)-3-(benzyloxy)-1-hydroxypropyl]-3,3-dimethylfuran-2,4(3H,5H)-dione
CAS No.:745818-75-1
Molecular Formula:C₁₆H₂₀O₅
Molecular Weight:292.332
Hs Code.:

Synonyms:(5R)-5-[(1S)-3-(benzyloxy)-1-hydroxypropyl]-3,3-dimethylfuran-2,4(3H,5H)-dione

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (5R)-5-[(1S)-3-(benzyloxy)-1-hydroxypropyl]-3,3-dimethylfuran-2,4(3H,5H)-dione

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Technology Process of (5R)-5-[(1S)-3-(benzyloxy)-1-hydroxypropyl]-3,3-dimethylfuran-2,4(3H,5H)-dione

There total 4 articles about (5R)-5-[(1S)-3-(benzyloxy)-1-hydroxypropyl]-3,3-dimethylfuran-2,4(3H,5H)-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:

: 745818-73-9
(E)-ethyl 7-(benzyloxy)-2,2-dimethyl-3-oxohept-4-enoate

: (5S)-5-[(1R)-3-(benzyloxy)-1-hydroxypropyl]-3,3-dimethylfuran-2,4(3H,5H)-dione

: 745818-75-1
(5R)-5-[(1S)-3-(benzyloxy)-1-hydroxypropyl]-3,3-dimethylfuran-2,4(3H,5H)-dione

Guidance literature:: With hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; sodium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; methanesulfonamide; In isopropyl alcohol; toluene; tert-butyl alcohol; at 0 ℃; for 17h; Title compound not separated from byproducts;
DOI:10.1055/s-2004-822389

Reference yield:

: 597-04-6
ethyl 2,2-dimethyl-3-oxobutanoate

: 745818-75-1
(5R)-5-[(1S)-3-(benzyloxy)-1-hydroxypropyl]-3,3-dimethylfuran-2,4(3H,5H)-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 75 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 85 percent / NEt₃; MsCl / CH₂Cl₂ / 3.5 h / 0 °C

3.1: OsO₄; (DHQD)2PHAL; K₃Fe(CN)6 / 2-methyl-propan-2-ol; H₂O / 17 h / 0 °C

With osmium(VIII) oxide; methanesulfonyl chloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III); lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2004.09.012

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 745818-75-1
(5R)-5-[(1S)-3-(benzyloxy)-1-hydroxypropyl]-3,3-dimethylfuran-2,4(3H,5H)-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 75 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 85 percent / NEt₃; MsCl / CH₂Cl₂ / 3.5 h / 0 °C

3.1: OsO₄; (DHQD)2PHAL; K₃Fe(CN)6 / 2-methyl-propan-2-ol; H₂O / 17 h / 0 °C

With osmium(VIII) oxide; methanesulfonyl chloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III); lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2004.09.012