(3R,4S,5R)-tert-butyl 3,4-bis(benzyloxy)-5-(hydroxymethyl)piperidine-1-carboxylate

Base Information

Chemical Name:(3R,4S,5R)-tert-butyl 3,4-bis(benzyloxy)-5-(hydroxymethyl)piperidine-1-carboxylate
CAS No.:1369810-75-2
Molecular Formula:C₂₅H₃₃NO₅
Molecular Weight:427.541
Hs Code.:

Synonyms:(3R,4S,5R)-tert-butyl 3,4-bis(benzyloxy)-5-(hydroxymethyl)piperidine-1-carboxylate

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Chemical Property of (3R,4S,5R)-tert-butyl 3,4-bis(benzyloxy)-5-(hydroxymethyl)piperidine-1-carboxylate

Chemical Property:

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Technology Process of (3R,4S,5R)-tert-butyl 3,4-bis(benzyloxy)-5-(hydroxymethyl)piperidine-1-carboxylate

There total 5 articles about (3R,4S,5R)-tert-butyl 3,4-bis(benzyloxy)-5-(hydroxymethyl)piperidine-1-carboxylate 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%

: 1369810-73-0
(3R,4S)-tert-butyl 3,4-bis(benzyloxy)-5-methylenepiperidine-1-carboxylate

: 1369810-75-2
(3R,4S,5R)-tert-butyl 3,4-bis(benzyloxy)-5-(hydroxymethyl)piperidine-1-carboxylate

Guidance literature:: (3R,4S)-tert-butyl 3,4-bis(benzyloxy)-5-methylenepiperidine-1-carboxylate; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 0 - 20 ℃;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 12h; stereoselective reaction;
DOI:10.1039/c2ob06851f

Reference yield:

: N-((4S,5R)-4,5-bis(benzyloxy)-3-methylenetetrahydro-2H-pyran-2-yl)-2,2,2-trichloroacetamide

: 1369810-75-2
(3R,4S,5R)-tert-butyl 3,4-bis(benzyloxy)-5-(hydroxymethyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C

2.1: sodium hydrogencarbonate / ethyl acetate / 4 h / 0 - 20 °C

3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

4.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C

5.2: 12 h / 0 - 20 °C

With sodium tetrahydroborate; potassium tert-butylate; sodium hydrogencarbonate; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;
DOI:10.1039/c2ob06851f

Reference yield:

: 1369810-71-8
(2R,3S)-2,3-bis(benzyloxy)-4-((tert-butoxycarbonylamino)methyl)pent-4-enyl methanesulfonate

: 1369810-75-2
(3R,4S,5R)-tert-butyl 3,4-bis(benzyloxy)-5-(hydroxymethyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C

2.2: 12 h / 0 - 20 °C

With potassium tert-butylate; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran;
DOI:10.1039/c2ob06851f