tert-butyl (3S)-3-<(2R,3R)-1-benzyloxycarbonyl-3-<(tert-butyldimethylsilyl)oxy>-2-pyrrolidinyl>-3-hydroxypropionate

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Chemical Name:tert-butyl (3S)-3-<(2R,3R)-1-benzyloxycarbonyl-3-<(tert-butyldimethylsilyl)oxy>-2-pyrrolidinyl>-3-hydroxypropionate
CAS No.:147428-95-3
Molecular Formula:C₂₅H₄₁NO₆Si
Molecular Weight:479.689
Hs Code.:

Synonyms:tert-butyl (3S)-3-<(2R,3R)-1-benzyloxycarbonyl-3-<(tert-butyldimethylsilyl)oxy>-2-pyrrolidinyl>-3-hydroxypropionate

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Chemical Property of tert-butyl (3S)-3-<(2R,3R)-1-benzyloxycarbonyl-3-<(tert-butyldimethylsilyl)oxy>-2-pyrrolidinyl>-3-hydroxypropionate

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Technology Process of tert-butyl (3S)-3-<(2R,3R)-1-benzyloxycarbonyl-3-<(tert-butyldimethylsilyl)oxy>-2-pyrrolidinyl>-3-hydroxypropionate

There total 9 articles about tert-butyl (3S)-3-<(2R,3R)-1-benzyloxycarbonyl-3-<(tert-butyldimethylsilyl)oxy>-2-pyrrolidinyl>-3-hydroxypropionate 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: 87.0%

: 150942-98-6
t-butyl lithioacetate

: 147428-94-2
(2R,3R)-N-benzyloxycarbonal-3-<(1,1-dimethylethyl)dimethylsilyl>oxy-2-prolinal

: 147428-95-3
tert-butyl (3S)-3-<(2R,3R)-1-benzyloxycarbonyl-3-<(tert-butyldimethylsilyl)oxy>-2-pyrrolidinyl>-3-hydroxypropionate

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(01)80323-9

Reference yield:

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

: 147428-95-3
tert-butyl (3S)-3-<(2R,3R)-1-benzyloxycarbonyl-3-<(tert-butyldimethylsilyl)oxy>-2-pyrrolidinyl>-3-hydroxypropionate

Guidance literature:: Multi-step reaction with 4 steps

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

2: 83 percent / aq. HOAc / tetrahydrofuran / 1) 0 deg C, 2 h, 2) RT, 10 h

3: 80 percent / SO₃*pyridine, NEt₃ / dimethylsulfoxide; CH₂Cl₂ / 6 h / Ambient temperature

4: 87 percent / tetrahydrofuran / 0.33 h / -78 °C

With 1H-imidazole; pyridine-SO₃ complex; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)80323-9

Reference yield:

: 84730-21-2
N-benzyloxycarbonyl-3,6-dideoxy-3,6-imino-1,2-O-isopropylidene-α-D-glucofuranose

: 147428-95-3
tert-butyl (3S)-3-<(2R,3R)-1-benzyloxycarbonyl-3-<(tert-butyldimethylsilyl)oxy>-2-pyrrolidinyl>-3-hydroxypropionate

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / 2,4,5-triiodoimidazole, PPh₃ / toluene / 4 h / Heating

2: 97 percent / Bu₃SnH, AIBN / benzene / 3 h / Heating

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

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

5: NaBH₄ / methanol / 10 h / Ambient temperature

6: 98 percent / imidazole / dimethylformamide / 1) 0 deg C, 30 min, 2) RT, 3 h

7: 83 percent / aq. HOAc / tetrahydrofuran / 1) 0 deg C, 2 h, 2) RT, 10 h

8: 80 percent / SO₃*pyridine, NEt₃ / dimethylsulfoxide; CH₂Cl₂ / 6 h / Ambient temperature

9: 87 percent / tetrahydrofuran / 0.33 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; 2,4,5-triiodoimidazole; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); Dowex 50X₄-400 ion exchange resin (H+); tri-n-butyl-tin hydride; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4020(01)80323-9