(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine

Base Information

• Chemical Name: (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine
• CAS No.: 944544-02-9
• Molecular Formula: C₂₇H₃₁NO₃
• Molecular Weight: 417.548

Synonyms:(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine

Chemical Property of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine

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Technology Process of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine

There total 13 articles about (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine 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: 55.0%

C27H29NO3 → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine (944544-02-9) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)piperidine (366815-76-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethyl acetate; for 12h; under 3750.38 Torr;

DOI:10.1021/ol990841e

Reference yield:

methylmagnesium bromide (75-16-1) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole (397242-80-7) → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine (944544-02-9) + (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine (944544-03-0)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -40 - 20 ℃;

DOI:10.1016/j.tet.2014.01.039

Reference yield:

C27H29N3O3 → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine (944544-02-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 124 mg / acetonitrile; CH₂Cl₂ / 3 h / 40 °C

2: 55 percent / H₂ / Pd(OH)2/C / ethyl acetate / 12 h / 3750.38 Torr

With hydrogen; palladium dihydroxide; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/ol990841e

upstream raw materials:

C₃₂H₃₉NO₆

(3S,4R,5R)-5-benzyloxymethyl-3,4-dibenzyloxy-1-(4-methoxybenzyl)-pyrrolidin-2-one

(3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one

(3S,4S)-1-(4-methoxybenzyl)-3,4-dibenzyloxy-2,5-pyrrolidinedione

Downstream raw materials:

(2R,3R,4R,5R)-3,4-dihydroxy-2-(hydroxymethyl)-5-methylpyrrolidine

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