(3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester
CAS No.:177420-28-9
Molecular Formula:C₂₄H₃₁NO₅
Molecular Weight:413.514
Hs Code.:

Synonyms:(3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

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Technology Process of (3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

There total 12 articles about (3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1-carboxylic acid tert-butyl 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: 75.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 177420-27-8
(3R,4R,5R)-3,4-di-O-benzyl-3,4,5-trihydroxypiperidine

: 177420-28-9
(3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With triethylamine; In methanol; for 8h; 0 deg C to room t.;
DOI:10.1016/0040-4039(96)00422-4

Reference yield:

: 177567-99-6
1,2,3-tri-O-acetyl-5-azido-5-deoxy-D-arabinofuranose

: 177420-28-9
(3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / TMSOTf / CH₂Cl₂ / 3 h / Ambient temperature

2: NaOMe, MeOH / 0.5 h / Ambient temperature

3: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, overnight

4: (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.08 h / 0 - 5 °C

5: H₂ / Pd-CaCO₃ / methanol / 24 h / Ambient temperature

6: 75 percent / Et₃N / methanol / 4 h / Ambient temperature

With methanol; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydride; triethylamine; Lindlar's catalyst; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja973443k

Reference yield:

: 100-39-0
benzyl bromide

: 177420-28-9
(3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, overnight

2: (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.08 h / 0 - 5 °C

3: H₂ / Pd-CaCO₃ / methanol / 24 h / Ambient temperature

4: 75 percent / Et₃N / methanol / 4 h / Ambient temperature

With ammonium cerium(IV) nitrate; hydrogen; sodium hydride; triethylamine; Lindlar's catalyst; In methanol; water; acetonitrile;
DOI:10.1021/ja973443k