(2R,3S)-3-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2R,3S)-3-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:899431-83-5
Molecular Formula:C₁₉H₂₅NO₇
Molecular Weight:379.41
Hs Code.:

Synonyms:(2R,3S)-3-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2R,3S)-3-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (2R,3S)-3-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

There total 12 articles about (2R,3S)-3-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester 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:

: 899431-78-8
(1R,2S)-1-Benzylamino-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-en-2-ol

: 899431-83-5
(2R,3S)-3-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: Hg(OAc)2 / tetrahydrofuran; H₂O / 3 h / 20 °C

1.2: sodium borohydride / tetrahydrofuran; H₂O

2.1: 0.48 g / TBAI / tetrahydrofuran; H₂O; various solvent(s) / 6 h / 0 - 20 °C

3.1: ammonium formate / Pd/C / methanol / 1 h / 80 °C

4.1: 0.09 g / sodium bicarbonate / methanol; H₂O / 3 h / 0 °C

With mercury(II) diacetate; ammonium formate; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo0601617

Reference yield:

: (2R,3S)-1-Benzyl-2-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidin-3-ol

: 899431-83-5
(2R,3S)-3-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 0.48 g / TBAI / tetrahydrofuran; H₂O; various solvent(s) / 6 h / 0 - 20 °C

2: ammonium formate / Pd/C / methanol / 1 h / 80 °C

3: 0.09 g / sodium bicarbonate / methanol; H₂O / 3 h / 0 °C

With ammonium formate; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo0601617

Reference yield:

: 899431-77-7
3-O-benzyl-1,2-O-isopropylidene-5,7,8-trideoxy-5-(N-benzylamino)-(5-N,6(S)-O-carbonyl)-α-L-glycero-D-gluco-7-eno-oct-1,4-furanose

: 899431-83-5
(2R,3S)-3-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 94 percent / aqueous KOH / methanol / 48 h / 90 °C

2.1: Hg(OAc)2 / tetrahydrofuran; H₂O / 3 h / 20 °C

2.2: sodium borohydride / tetrahydrofuran; H₂O

3.1: 0.48 g / TBAI / tetrahydrofuran; H₂O; various solvent(s) / 6 h / 0 - 20 °C

4.1: ammonium formate / Pd/C / methanol / 1 h / 80 °C

5.1: 0.09 g / sodium bicarbonate / methanol; H₂O / 3 h / 0 °C

With potassium hydroxide; mercury(II) diacetate; ammonium formate; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo0601617