(2R,3R)-N-benzyloxycarbonyl-3-<(1,1-dimethylethyl)dimethylsilyl>oxy-2-<(1,1-dimethylethyl)dimethylsilyl>oxymethylpyrrolidine

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Chemical Name:(2R,3R)-N-benzyloxycarbonyl-3-<(1,1-dimethylethyl)dimethylsilyl>oxy-2-<(1,1-dimethylethyl)dimethylsilyl>oxymethylpyrrolidine
CAS No.:147428-92-0
Molecular Formula:C₂₅H₄₅NO₄Si₂
Molecular Weight:479.808
Hs Code.:

Synonyms:(2R,3R)-N-benzyloxycarbonyl-3-<(1,1-dimethylethyl)dimethylsilyl>oxy-2-<(1,1-dimethylethyl)dimethylsilyl>oxymethylpyrrolidine

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Chemical Property of (2R,3R)-N-benzyloxycarbonyl-3-<(1,1-dimethylethyl)dimethylsilyl>oxy-2-<(1,1-dimethylethyl)dimethylsilyl>oxymethylpyrrolidine

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Technology Process of (2R,3R)-N-benzyloxycarbonyl-3-<(1,1-dimethylethyl)dimethylsilyl>oxy-2-<(1,1-dimethylethyl)dimethylsilyl>oxymethylpyrrolidine

There total 15 articles about (2R,3R)-N-benzyloxycarbonyl-3-<(1,1-dimethylethyl)dimethylsilyl>oxy-2-<(1,1-dimethylethyl)dimethylsilyl>oxymethylpyrrolidine 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: 98.0%

: 133161-12-3
(2R,3R)-1-(Benzyloxycarbonyl)-3-hydroxy-2-(hydroxymethyl)pyrrolidine

: 18162-48-6
tert-butyldimethylsilyl chloride

: 147428-92-0
(2R,3R)-N-benzyloxycarbonyl-3-<(1,1-dimethylethyl)dimethylsilyl>oxy-2-<(1,1-dimethylethyl)dimethylsilyl>oxymethylpyrrolidine

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; 1) 0 deg C, 30 min, 2) RT, 3 h;
DOI:10.1016/S0040-4020(01)80323-9

Reference yield:

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

: 147428-92-0
(2R,3R)-N-benzyloxycarbonyl-3-<(1,1-dimethylethyl)dimethylsilyl>oxy-2-<(1,1-dimethylethyl)dimethylsilyl>oxymethylpyrrolidine

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: Dowex 50X₄-400 ion exchange resin (H+) / H₂O; dioxane / 48 h / 40 °C

11: NaIO₄ / dioxane; H₂O / 3.5 h / 0 °C

12: NaBH₄ / methanol / 10 h / Ambient temperature

13: 98 percent / imidazole / dimethylformamide / 1) 0 deg C, 30 min, 2) RT, 3 h

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; 2,4,5-triiodoimidazole; sodium azide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; Dowex 50X₄-400 ion exchange resin (H+); sulfuric acid; hydrogen; tri-n-butyl-tin hydride; sodium acetate; sodium carbonate; triphenylphosphine; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; 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

: 147428-92-0
(2R,3R)-N-benzyloxycarbonyl-3-<(1,1-dimethylethyl)dimethylsilyl>oxy-2-<(1,1-dimethylethyl)dimethylsilyl>oxymethylpyrrolidine

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: Dowex 50X₄-400 ion exchange resin (H+) / H₂O; dioxane / 48 h / 40 °C

12: NaIO₄ / dioxane; H₂O / 3.5 h / 0 °C

13: NaBH₄ / methanol / 10 h / Ambient temperature

14: 98 percent / imidazole / dimethylformamide / 1) 0 deg C, 30 min, 2) RT, 3 h

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; 2,4,5-triiodoimidazole; sodium azide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; Dowex 50X₄-400 ion exchange resin (H+); sulfuric acid; hydrogen; tri-n-butyl-tin hydride; sodium acetate; sodium carbonate; triphenylphosphine; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1016/S0040-4020(01)80323-9