(-)-(2S,3R)-1-<(benzyloxy)carbonyl>-2-<(S)-1-(benzyloxy)prop-2-enyl>-3-hydroxypyrrolidine

Base Information

Chemical Name:(-)-(2S,3R)-1-<(benzyloxy)carbonyl>-2-<(S)-1-(benzyloxy)prop-2-enyl>-3-hydroxypyrrolidine
CAS No.:98944-26-4
Molecular Formula:C₂₂H₂₅NO₄
Molecular Weight:367.445
Hs Code.:

Synonyms:(-)-(2S,3R)-1-<(benzyloxy)carbonyl>-2-<(S)-1-(benzyloxy)prop-2-enyl>-3-hydroxypyrrolidine

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Chemical Property of (-)-(2S,3R)-1-<(benzyloxy)carbonyl>-2-<(S)-1-(benzyloxy)prop-2-enyl>-3-hydroxypyrrolidine

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Technology Process of (-)-(2S,3R)-1-<(benzyloxy)carbonyl>-2-<(S)-1-(benzyloxy)prop-2-enyl>-3-hydroxypyrrolidine

There total 15 articles about (-)-(2S,3R)-1-<(benzyloxy)carbonyl>-2-<(S)-1-(benzyloxy)prop-2-enyl>-3-hydroxypyrrolidine 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: 71.0%

: (1R,4R,5S)-4-(benzyloxy)-5-<(benzyloxy)carbonyl>-2-oxa-6-azabicyclo<3.3.0>octan-3-ol

: 19493-09-5
Methylenetriphenylphosphorane

: 98944-26-4
(-)-(2S,3R)-1-<(benzyloxy)carbonyl>-2-<(S)-1-(benzyloxy)prop-2-enyl>-3-hydroxypyrrolidine

Guidance literature:: In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)92511-5

Reference yield:

: 14686-89-6
(1,2:5,6)-di-O-isopropylidene-D-gulose

: 98944-26-4
(-)-(2S,3R)-1-<(benzyloxy)carbonyl>-2-<(S)-1-(benzyloxy)prop-2-enyl>-3-hydroxypyrrolidine

Guidance literature:: Multi-step reaction with 13 steps

1: 95 percent / pyridine

2: 74 percent / 0.8percent aq. H₂SO₄ / dioxane; methanol / 23 h / Ambient temperature

3: 94 percent / CBr₄, PPh₃ / tetrahydrofuran / 11 h / Ambient temperature

4: 96 percent / NaN₃ / dimethylformamide / 8 h / 45 °C

5: H₂ / Raney nickel / methanol / 24 h / Ambient temperature

6: NaOAc / ethanol / 15 h / Heating

7: Na₂CO₃ / acetone; H₂O / 2 h / 0 °C

8: 99 percent / 2,4,5-triiodoimidazole, PPh₃ / toluene / 4 h / Heating

9: 97 percent / Bu₃SnH, AIBN / benzene / 3 h / Heating

10: 94 percent / HCl / diethyl ether / 15 h / Ambient temperature

11: 1) KH / 1) DMF, RT, 30 min

12: 86 percent / 50percent aq. TFA / 5 h / 50 °C

13: 1) n-BuLi / 1) THF, hexane, RT, 2) THF, 45 deg C, 5 h

With pyridine; hydrogenchloride; 2,4,5-triiodoimidazole; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; sulfuric acid; hydrogen; tri-n-butyl-tin hydride; sodium acetate; potassium hydride; sodium carbonate; triphenylphosphine; trifluoroacetic acid; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1016/S0040-4020(01)80323-9

Reference yield:

: 2847-00-9
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

: 98944-26-4
(-)-(2S,3R)-1-<(benzyloxy)carbonyl>-2-<(S)-1-(benzyloxy)prop-2-enyl>-3-hydroxypyrrolidine

Guidance literature:: Multi-step reaction with 14 steps

1: NaBH₄ / ethanol

2: 95 percent / pyridine

3: 74 percent / 0.8percent aq. H₂SO₄ / dioxane; methanol / 23 h / Ambient temperature

4: 94 percent / CBr₄, PPh₃ / tetrahydrofuran / 11 h / Ambient temperature

5: 96 percent / NaN₃ / dimethylformamide / 8 h / 45 °C

6: H₂ / Raney nickel / methanol / 24 h / Ambient temperature

7: NaOAc / ethanol / 15 h / Heating

8: Na₂CO₃ / acetone; H₂O / 2 h / 0 °C

9: 99 percent / 2,4,5-triiodoimidazole, PPh₃ / toluene / 4 h / Heating

10: 97 percent / Bu₃SnH, AIBN / benzene / 3 h / Heating

11: 94 percent / HCl / diethyl ether / 15 h / Ambient temperature

12: 1) KH / 1) DMF, RT, 30 min

13: 86 percent / 50percent aq. TFA / 5 h / 50 °C

14: 1) n-BuLi / 1) THF, hexane, RT, 2) THF, 45 deg C, 5 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; 2,4,5-triiodoimidazole; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; sulfuric acid; hydrogen; tri-n-butyl-tin hydride; sodium acetate; potassium hydride; sodium carbonate; triphenylphosphine; trifluoroacetic acid; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1016/S0040-4020(01)80323-9