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

Base Information

Chemical Name:(3R,4S,5R)-tert-butyl 4,5-bis(benzyloxy)-3-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate
CAS No.:1369810-92-3
Molecular Formula:C₂₅H₃₃NO₆
Molecular Weight:443.54
Hs Code.:

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

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

Chemical Property:

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

There total 5 articles about (3R,4S,5R)-tert-butyl 4,5-bis(benzyloxy)-3-hydroxy-3-(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: 82.0%

: 177420-29-0
(3R,4R)-tert-butyl 3,4-bis(benzyloxy)-5-methylenepiperidine-1-carboxylate

: 1369810-92-3
(3R,4S,5R)-tert-butyl 4,5-bis(benzyloxy)-3-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

: 1369810-93-4
(3S,4S,5R)-tert-butyl 4,5-bis(benzyloxy)-3-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

Guidance literature:: With osmium(VIII) oxide; water; In 1-methyl-pyrrolidin-2-one; acetone; tert-butyl alcohol; at 20 ℃; for 48h;
DOI:10.1039/c2ob06851f

Reference yield:

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

: 1369810-92-3
(3R,4S,5R)-tert-butyl 4,5-bis(benzyloxy)-3-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

: 1369810-93-4
(3S,4S,5R)-tert-butyl 4,5-bis(benzyloxy)-3-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

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

5: osmium(VIII) oxide; water / acetone; tert-butyl alcohol; 1-methyl-pyrrolidin-2-one / 48 h / 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; potassium tert-butylate; water; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; ethyl acetate; acetone; tert-butyl alcohol;
DOI:10.1039/c2ob06851f

Reference yield:

: 1369810-85-4
tert-butyl (3R,4R)-3,4-bis(benzyloxy)-5-hydroxy-2-methylenepentylcarbamate

: 1369810-92-3
(3R,4S,5R)-tert-butyl 4,5-bis(benzyloxy)-3-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

: 1369810-93-4
(3S,4S,5R)-tert-butyl 4,5-bis(benzyloxy)-3-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: osmium(VIII) oxide; water / acetone; tert-butyl alcohol; 1-methyl-pyrrolidin-2-one / 48 h / 20 °C

With osmium(VIII) oxide; potassium tert-butylate; water; triethylamine; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; acetone; tert-butyl alcohol;
DOI:10.1039/c2ob06851f