benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate

Base Information

Chemical Name:benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate
CAS No.:1277172-78-7
Molecular Formula:C₃₅H₃₇NO₆
Molecular Weight:567.682
Hs Code.:

Synonyms:benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate

Chemical Property:

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Technology Process of benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate

There total 12 articles about benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(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: 86.0%

: 1277172-76-5
benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(trityloxymethyl)piperidine-1-carboxylate

: 1277172-78-7
benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 1h;
DOI:10.1002/ejoc.201001171

Reference yield:

: 1277172-60-7
(2S,3S)-2-azido-3-(benzyloxy)-1-(trityloxy)pent-4-ene

: 1277172-78-7
benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C

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

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C

3.2: 2 h

4.1: Grubbs catalyst first generation / dichloromethane / 12 h / 20 °C

5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 20 °C

6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

6.2: 8 h / 20 °C

7.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

With Grubbs catalyst first generation; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol;
DOI:10.1002/ejoc.201001171

Reference yield:

: C₃₁H₃₁NO₂

: 1277172-78-7
benzyl (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydrogencarbonate / ethyl acetate / 4 h / 0 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C

2.2: 2 h

3.1: Grubbs catalyst first generation / dichloromethane / 12 h / 20 °C

4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

5.2: 8 h / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

With Grubbs catalyst first generation; osmium(VIII) oxide; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; trifluoroacetic acid; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol;
DOI:10.1002/ejoc.201001171