(+)-(2R,3R,4R,5R)-5-[(1R)-1,3-dihydroxypropyl]-2-(phenylmethoxy)methylpyrrolizine-3,4-diol

Base Information

Chemical Name:(+)-(2R,3R,4R,5R)-5-[(1R)-1,3-dihydroxypropyl]-2-(phenylmethoxy)methylpyrrolizine-3,4-diol
CAS No.:618384-80-8
Molecular Formula:C₁₅H₂₃NO₅
Molecular Weight:297.351
Hs Code.:

Synonyms:(+)-(2R,3R,4R,5R)-5-[(1R)-1,3-dihydroxypropyl]-2-(phenylmethoxy)methylpyrrolizine-3,4-diol

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Chemical Property of (+)-(2R,3R,4R,5R)-5-[(1R)-1,3-dihydroxypropyl]-2-(phenylmethoxy)methylpyrrolizine-3,4-diol

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Technology Process of (+)-(2R,3R,4R,5R)-5-[(1R)-1,3-dihydroxypropyl]-2-(phenylmethoxy)methylpyrrolizine-3,4-diol

There total 13 articles about (+)-(2R,3R,4R,5R)-5-[(1R)-1,3-dihydroxypropyl]-2-(phenylmethoxy)methylpyrrolizine-3,4-diol 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: 61.0%

: (+)-(1R,5R,6R,7R,7aR)-6-hydroxyl-1-(2-hydroxy)ethyl-7-phenylcarbonyloxy-5-phenylmethoxymethyltetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one

: 618384-80-8
(+)-(2R,3R,4R,5R)-5-[(1R)-1,3-dihydroxypropyl]-2-(phenylmethoxy)methylpyrrolizine-3,4-diol

Guidance literature:: With sodium hydroxide; In ethanol; at 70 ℃; for 24h;
DOI:10.1021/jo034914q

Reference yield:

: 146916-76-9
5-(4-methoxyphenyl)methoxy-2-pentyn-1-ol

: 618384-80-8
(+)-(2R,3R,4R,5R)-5-[(1R)-1,3-dihydroxypropyl]-2-(phenylmethoxy)methylpyrrolizine-3,4-diol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 89 percent / Red-Al / tetrahydrofuran; toluene / 4 h / 20 °C

2.1: T-BuOOH; CaH₂; D-(-)-diisopropyl tartrate / silica gel; Ti(O-i-Pr)4 / CH₂Cl₂ / 24 h / -20 °C

3.1: Et₃N; DMSO; (COCl)2 / CH₂Cl₂ / 0.42 h / -60 - 20 °C

4.1: 1.51 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 2 h / -10 °C

5.1: 98 percent / lithium triflate / acetonitrile / 72 h / 120 °C

6.1: 79 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

7.1: 82 percent / 4-morpholine N-oxide; K₂OsO₄*2H₂O / acetone; H₂O / 24 h / 20 °C

8.1: SOCl₂; Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

9.1: 31.3 mg / RuCl₃*3H₂O; NaIO₄ / acetonitrile; CCl₄; H₂O / 1.5 h / 20 °C

10.1: Cs₂CO₃ / dimethylformamide / 4 h / 40 °C

10.2: 56 percent / aq. H₂SO₄ / tetrahydrofuran / 22 h / 20 °C

11.1: 75 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H₂O / CH₂Cl₂ / 3 h / 20 °C

12.1: 61 percent / NaOH / ethanol / 24 h / 70 °C

With tert.-butylhydroperoxide; ruthenium trichloride; sodium hydroxide; potassium osmate(VI); sodium periodate; thionyl chloride; calcium hydride; oxalyl dichloride; water; potassium hexamethylsilazane; lithium trifluoromethanesulfonate; D-(-)-diisopropyl tartrate; caesium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; silica gel; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 3.1: Swern oxidation / 4.1: Wittig olefination;
DOI:10.1021/jo034914q

Reference yield:

: 158817-21-1
(E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol

: 618384-80-8
(+)-(2R,3R,4R,5R)-5-[(1R)-1,3-dihydroxypropyl]-2-(phenylmethoxy)methylpyrrolizine-3,4-diol

Guidance literature:: Multi-step reaction with 11 steps

1.1: T-BuOOH; CaH₂; D-(-)-diisopropyl tartrate / silica gel; Ti(O-i-Pr)4 / CH₂Cl₂ / 24 h / -20 °C

2.1: Et₃N; DMSO; (COCl)2 / CH₂Cl₂ / 0.42 h / -60 - 20 °C

3.1: 1.51 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 2 h / -10 °C

4.1: 98 percent / lithium triflate / acetonitrile / 72 h / 120 °C

5.1: 79 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

6.1: 82 percent / 4-morpholine N-oxide; K₂OsO₄*2H₂O / acetone; H₂O / 24 h / 20 °C

7.1: SOCl₂; Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

8.1: 31.3 mg / RuCl₃*3H₂O; NaIO₄ / acetonitrile; CCl₄; H₂O / 1.5 h / 20 °C

9.1: Cs₂CO₃ / dimethylformamide / 4 h / 40 °C

9.2: 56 percent / aq. H₂SO₄ / tetrahydrofuran / 22 h / 20 °C

10.1: 75 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H₂O / CH₂Cl₂ / 3 h / 20 °C

11.1: 61 percent / NaOH / ethanol / 24 h / 70 °C

With tert.-butylhydroperoxide; ruthenium trichloride; sodium hydroxide; potassium osmate(VI); sodium periodate; thionyl chloride; calcium hydride; oxalyl dichloride; water; potassium hexamethylsilazane; lithium trifluoromethanesulfonate; D-(-)-diisopropyl tartrate; caesium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; silica gel; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 2.1: Swern oxidation / 3.1: Wittig olefination;
DOI:10.1021/jo034914q