(2S,3S,4R,5S)-tert-btyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

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Chemical Name:(2S,3S,4R,5S)-tert-btyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate
CAS No.:1454797-37-5
Molecular Formula:C₃₂H₃₉NO₆
Molecular Weight:533.665
Hs Code.:

Synonyms:(2S,3S,4R,5S)-tert-btyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

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Chemical Property of (2S,3S,4R,5S)-tert-btyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

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Technology Process of (2S,3S,4R,5S)-tert-btyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

There total 5 articles about (2S,3S,4R,5S)-tert-btyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(hydroxymethyl)pyrrolidine-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: 81.0%

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

: 1454797-33-1
((2S,3R,4S,5S)-1-benzyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-pyrrolidin-2-yl)methanol

: 1454797-37-5
(2S,3S,4R,5S)-tert-btyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

Guidance literature:: With sodium carbonate; In ethyl acetate; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jo401613v

Reference yield:

: 1454797-10-4
(2R,3S,4S)-1,3,4-tris(benzyloxy)-5-oxo-6-(trityloxy)hexan-2-yl formate

: 1454797-37-5
(2S,3S,4R,5S)-tert-btyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium tetrahydroborate / methanol / 1.25 h / 0 °C / Inert atmosphere

2: triethylamine; dmap / dichloromethane / 1 h / 0 °C / Inert atmosphere

3: 6 h / 140 °C / Inert atmosphere

4: trifluoroacetic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

5: sodium carbonate / ethyl acetate / 3 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; sodium carbonate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; ethyl acetate;
DOI:10.1021/jo401613v

Reference yield:

: 1454797-28-4
(2R,3S,4R,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diol

: 1454797-37-5
(2S,3S,4R,5S)-tert-btyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine; dmap / dichloromethane / 1 h / 0 °C / Inert atmosphere

2: 6 h / 140 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

4: sodium carbonate / ethyl acetate / 3 h / 20 °C / Inert atmosphere

With dmap; sodium carbonate; triethylamine; trifluoroacetic acid; In dichloromethane; ethyl acetate;
DOI:10.1021/jo401613v