(2S,3S,4R)-<1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone

Base Information

Chemical Name:(2S,3S,4R)-<1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone
CAS No.:115890-48-7
Molecular Formula:C₂₄H₃₇NO₅Si
Molecular Weight:447.647
Hs Code.:

Synonyms:(2S,3S,4R)-<1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone

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Chemical Property of (2S,3S,4R)-<1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone

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Technology Process of (2S,3S,4R)-<1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone

There total 8 articles about (2S,3S,4R)-<1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone 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: 83.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 115890-44-3
(2S,3S,4R)-<1-(benzyloxycarbonyl)-2-(hydroxymethyl)-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone

: 115890-48-7
(2S,3S,4R)-<1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 25h; Ambient temperature;
DOI:10.1021/ja00227a029

Reference yield:

: 115890-38-5
((R)-2-Benzyloxy-1-formyl-ethyl)-(3-methyl-but-2-enyl)-carbamic acid benzyl ester

: 115890-48-7
(2S,3S,4R)-<1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone

Guidance literature:: Multi-step reaction with 4 steps

1: 4.24 g / ethylenediammonium diacetate / propan-2-ol / 16 h / Ambient temperature

2: 2.27 g / H₂O / dioxane / 15 h / Heating

3: 41 percent / BBr₃ / CH₂Cl₂ / 1.) -40 deg C to 0 deg C, 1 h, 2.) 0 deg C, 30 min

4: 83 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 25 h / Ambient temperature

With dmap; water; boron tribromide; ethylenediamine diacetic acid; triethylamine; In 1,4-dioxane; dichloromethane; isopropyl alcohol;
DOI:10.1021/ja00227a029

Reference yield:

: (2R,3RS)-2-<(benzyloxycarbonyl)prenylamino>-1-(benzyloxy)-3,4-butandiol

: 115890-48-7
(2S,3S,4R)-<1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone

Guidance literature:: Multi-step reaction with 5 steps

1: 3.27 g / NaIO₄ / methanol; H₂O / 2 h / 0 °C

2: 4.24 g / ethylenediammonium diacetate / propan-2-ol / 16 h / Ambient temperature

3: 2.27 g / H₂O / dioxane / 15 h / Heating

4: 41 percent / BBr₃ / CH₂Cl₂ / 1.) -40 deg C to 0 deg C, 1 h, 2.) 0 deg C, 30 min

5: 83 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 25 h / Ambient temperature

With dmap; sodium periodate; water; boron tribromide; ethylenediamine diacetic acid; triethylamine; In 1,4-dioxane; methanol; dichloromethane; water; isopropyl alcohol;
DOI:10.1021/ja00227a029