(3S,5S)-3-(benzylamino)-1-[(benzyloxy)carbonyl]-5-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: (3S,5S)-3-(benzylamino)-1-[(benzyloxy)carbonyl]-5-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid
• CAS No.: 1205681-44-2
• Molecular Formula: C₂₅H₃₀N₂O₆
• Molecular Weight: 454.523

Synonyms:(3S,5S)-3-(benzylamino)-1-[(benzyloxy)carbonyl]-5-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid

Chemical Property of (3S,5S)-3-(benzylamino)-1-[(benzyloxy)carbonyl]-5-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid

Chemical Property:

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Technology Process of (3S,5S)-3-(benzylamino)-1-[(benzyloxy)carbonyl]-5-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid

There total 4 articles about (3S,5S)-3-(benzylamino)-1-[(benzyloxy)carbonyl]-5-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid 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%

benzaldehyde (100-52-7) + (3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-aminopyrrolidine-3-carboxylic acid (526222-99-1) → (3S,5S)-3-(benzylamino)-1-[(benzyloxy)carbonyl]-5-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid (1205681-44-2)

Guidance literature:

benzaldehyde; (3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-aminopyrrolidine-3-carboxylic acid; In methanol; at 20 ℃; for 0.5h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 12h;

DOI:10.1021/ja3069648

Reference yield:

C25H28N2O6 → (3S,5S)-3-(benzylamino)-1-[(benzyloxy)carbonyl]-5-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid (1205681-44-2)

Guidance literature:

With sodium cyanoborohydride; In methanol; at 20 ℃;

DOI:10.1021/ol100048g

Reference yield:

(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-aminopyrrolidine-3-carboxylic acid (526222-99-1) → (3S,5S)-3-(benzylamino)-1-[(benzyloxy)carbonyl]-5-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid (1205681-44-2)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol / 0.5 h / 25 °C

2: sodium cyanoborohydride / 20 h / 25 °C

With sodium cyanoborohydride; In methanol;

DOI:10.1021/jo300569c

upstream raw materials:

benzaldehyde

(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-aminopyrrolidine-3-carboxylic acid

Downstream raw materials:

C₃₀H₃₂N₆O₆

(3'S,4S,9'S,11'S)-3-benzyl-3''-{[2-(hydroxymethyl)phenyl]methyl}-1''-(naphthalen-1-yl)-1-phenyldispiro[imidazolidine-4,5'-[1,7]diazatricyclo[7.3.0.0^3,7]dodecane-11',4''-imidazolidine]-2,2'2'',5,5'',8'-hexone

7-benzyl-8-tert-butyl (5S,8S)-1-benzyl-2,4-dioxo-3-phenyl-1,3,7-triazaspiro[4,4]nonane-7,8-dicarboxylate

(3S,5S)-6-benzyl-8,8-dimethyl-9-(naphthalen-1-ylmethyl)-7,10-dioxo-2,6,9-triazaspiro[4,5]decane-3-carboxylic acid trifluoroacetic acid

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