(5R)-5-[(1S,2R,3R)-4-(N,N-dibenzylamino)-1-hydroxy-2,3-isopropylidenedioxybutyl]tetrahydrofuran-2-one

Base Information

Chemical Name:(5R)-5-[(1S,2R,3R)-4-(N,N-dibenzylamino)-1-hydroxy-2,3-isopropylidenedioxybutyl]tetrahydrofuran-2-one
CAS No.:496771-91-6
Molecular Formula:C₂₅H₃₁NO₅
Molecular Weight:425.525
Hs Code.:

Synonyms:(5R)-5-[(1S,2R,3R)-4-(N,N-dibenzylamino)-1-hydroxy-2,3-isopropylidenedioxybutyl]tetrahydrofuran-2-one

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Chemical Property of (5R)-5-[(1S,2R,3R)-4-(N,N-dibenzylamino)-1-hydroxy-2,3-isopropylidenedioxybutyl]tetrahydrofuran-2-one

Chemical Property:

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Technology Process of (5R)-5-[(1S,2R,3R)-4-(N,N-dibenzylamino)-1-hydroxy-2,3-isopropylidenedioxybutyl]tetrahydrofuran-2-one

There total 5 articles about (5R)-5-[(1S,2R,3R)-4-(N,N-dibenzylamino)-1-hydroxy-2,3-isopropylidenedioxybutyl]tetrahydrofuran-2-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: 60.0%

: 496771-89-2
methyl (E)-(6S,7R)-8-(N,N-dibenzylamino)-6,7-isopropylidenedioxy-4-octenoate

: (5S)-5-[(1R,2R,3R)-4-(N,N-dibenzylamino)-1-hydroxy-2,3-isopropylidenedioxybutyl]tetrahydrofuran-2-one

: 496771-91-6
(5R)-5-[(1S,2R,3R)-4-(N,N-dibenzylamino)-1-hydroxy-2,3-isopropylidenedioxybutyl]tetrahydrofuran-2-one

Guidance literature:: With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); potassium osmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 20 ℃; for 48h;
DOI:10.3987/com-02-s(m)40

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 496771-91-6
(5R)-5-[(1S,2R,3R)-4-(N,N-dibenzylamino)-1-hydroxy-2,3-isopropylidenedioxybutyl]tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / tetrahydrofuran / 12 h / 20 °C

2.1: 96 percent / aq. sodium periodate; silica gel / CH₂Cl₂ / 1.5 h / 20 °C

3.1: glacial acetic acid; sodium cyanoborohydride / methanol / 72 h / 20 °C

3.2: pyridine; acetic anhydride / 3 h / 20 °C

3.3: 99 percent / aq. K₂CO₃ / methanol / 12 h

4.1: 44.1 g / propionic acid / toluene / 16 h / Heating

5.1: 60 percent / potassium ferricyanide; potassium carbonate; methanesulfonamide / potassium osmate dihydrate; (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 48 h / 20 °C

With sodium periodate; methanesulfonamide; silica gel; sodium cyanoborohydride; potassium carbonate; acetic acid; propionic acid; potassium hexacyanoferrate(III); potassium osmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol; 4.1: Claisen rearrangement / 5.1: Sharpless asymmetric dihydroxylation;
DOI:10.3987/com-02-s(m)40

Reference yield:

: 141436-58-0,126113-84-6
(-)-(1R)-1-[(4R,5S)-5-((1S)-1-hydroxyallyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol

: 496771-91-6
(5R)-5-[(1S,2R,3R)-4-(N,N-dibenzylamino)-1-hydroxy-2,3-isopropylidenedioxybutyl]tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / aq. sodium periodate; silica gel / CH₂Cl₂ / 1.5 h / 20 °C

2.1: glacial acetic acid; sodium cyanoborohydride / methanol / 72 h / 20 °C

2.2: pyridine; acetic anhydride / 3 h / 20 °C

2.3: 99 percent / aq. K₂CO₃ / methanol / 12 h

3.1: 44.1 g / propionic acid / toluene / 16 h / Heating

4.1: 60 percent / potassium ferricyanide; potassium carbonate; methanesulfonamide / potassium osmate dihydrate; (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 48 h / 20 °C

With sodium periodate; methanesulfonamide; silica gel; sodium cyanoborohydride; potassium carbonate; acetic acid; propionic acid; potassium hexacyanoferrate(III); potassium osmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; In methanol; dichloromethane; water; toluene; tert-butyl alcohol; 3.1: Claisen rearrangement / 4.1: Sharpless asymmetric dihydroxylation;
DOI:10.3987/com-02-s(m)40