(2R,3R)-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

Base Information

Chemical Name:(2R,3R)-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
CAS No.:899431-73-3
Molecular Formula:C₂₅H₃₁NO₅
Molecular Weight:425.525
Hs Code.:

Synonyms:(2R,3R)-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

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Chemical Property of (2R,3R)-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

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Technology Process of (2R,3R)-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

There total 9 articles about (2R,3R)-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 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: 74.0%

: 899431-72-2
(1R,2R)-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

: 899431-73-3
(2R,3R)-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

Guidance literature:: (1R,2R)-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; With mercury(II) diacetate; In tetrahydrofuran; water; at 20 ℃; for 3h;

With sodium tetrahydroborate; In tetrahydrofuran; water;
DOI:10.1021/jo0601617

Reference yield:

: 899431-71-1
(4R,5R)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-oxazolidin-2-one

: 899431-73-3
(2R,3R)-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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / aqueous KOH / methanol / 48 h / 90 °C

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

2.2: 74 percent / sodium borohydride / tetrahydrofuran; H₂O

With potassium hydroxide; mercury(II) diacetate; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo0601617

Reference yield:

: Benzyl-[(S)-1-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

: 899431-73-3
(2R,3R)-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

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2.90 g / sodium metaperiodate / acetone; H₂O / 6 h

2.1: tetrahydrofuran / 1 h / -50 °C

3.1: 1.2 g / aq. KOH / methanol / 0.17 h / 90 °C

4.1: 98 percent / aqueous KOH / methanol / 48 h / 90 °C

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

5.2: 74 percent / sodium borohydride / tetrahydrofuran; H₂O

With potassium hydroxide; sodium periodate; mercury(II) diacetate; In tetrahydrofuran; methanol; water; acetone; 2.1: Grignard reaction;
DOI:10.1021/jo0601617