(2R,3R,4R,5S)-2-(benzyloxymethyl)-5-(4-benzyloxyphenyl)-3,4-dibenzyloxy-pyrrolidine

Base Information

Chemical Name:(2R,3R,4R,5S)-2-(benzyloxymethyl)-5-(4-benzyloxyphenyl)-3,4-dibenzyloxy-pyrrolidine
CAS No.:944544-10-9
Molecular Formula:C₃₉H₃₉NO₄
Molecular Weight:585.743
Hs Code.:

Synonyms:(2R,3R,4R,5S)-2-(benzyloxymethyl)-5-(4-benzyloxyphenyl)-3,4-dibenzyloxy-pyrrolidine

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Chemical Property of (2R,3R,4R,5S)-2-(benzyloxymethyl)-5-(4-benzyloxyphenyl)-3,4-dibenzyloxy-pyrrolidine

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Technology Process of (2R,3R,4R,5S)-2-(benzyloxymethyl)-5-(4-benzyloxyphenyl)-3,4-dibenzyloxy-pyrrolidine

There total 8 articles about (2R,3R,4R,5S)-2-(benzyloxymethyl)-5-(4-benzyloxyphenyl)-3,4-dibenzyloxy-pyrrolidine 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: 58.0%

: 944544-00-7
(3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one

: 120186-59-6
(4-(benzyloxy)phenyl)magnesium bromide

: 944544-10-9
(2R,3R,4R,5S)-2-(benzyloxymethyl)-5-(4-benzyloxyphenyl)-3,4-dibenzyloxy-pyrrolidine

Guidance literature:: (3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one; (4-(benzyloxy)phenyl)magnesium bromide; In diethyl ether; dichloromethane; at -20 ℃; for 2h;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; Further stages.;
DOI:10.1016/j.tet.2007.02.087

Reference yield:

: 944543-93-5
(3S,4R,5R)-5-benzyloxymethyl-3,4-dibenzyloxy-1-(4-methoxybenzyl)-pyrrolidin-2-one

: 944544-10-9
(2R,3R,4R,5S)-2-(benzyloxymethyl)-5-(4-benzyloxyphenyl)-3,4-dibenzyloxy-pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 85 percent / ceric ammonium nitrate / acetonitrile; H₂O / 5.5 h / 0 - 20 °C

2.1: 95 percent / 4-(dimethylamino)pyridine; NEt₃ / CH₂Cl₂ / 4 h / 20 °C

3.1: CH₂Cl₂; diethyl ether / 2 h / -20 °C

3.2: 58 percent / triethylsilane; boron trifluoride etherate / CH₂Cl₂ / -78 - 20 °C

With dmap; ammonium cerium(IV) nitrate; triethylamine; In diethyl ether; dichloromethane; water; acetonitrile; 3.1: Grignard reaction;
DOI:10.1016/j.tet.2007.02.087

Reference yield:

: 944543-96-8
(3S,4S)-1-(4-methoxybenzyl)-3,4-dibenzyloxy-2,5-pyrrolidinedione

: 944544-10-9
(2R,3R,4R,5S)-2-(benzyloxymethyl)-5-(4-benzyloxyphenyl)-3,4-dibenzyloxy-pyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 81 percent / magnesium; mercury(II) chloride / tetrahydrofuran / 7 h / 20 °C

2.1: 777 mg / triethylsilane; boron trifluoride etherate / CH₂Cl₂ / -78 - 20 °C

3.1: 85 percent / ceric ammonium nitrate / acetonitrile; H₂O / 5.5 h / 0 - 20 °C

4.1: 95 percent / 4-(dimethylamino)pyridine; NEt₃ / CH₂Cl₂ / 4 h / 20 °C

5.1: CH₂Cl₂; diethyl ether / 2 h / -20 °C

5.2: 58 percent / triethylsilane; boron trifluoride etherate / CH₂Cl₂ / -78 - 20 °C

With triethylsilane; dmap; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; magnesium; triethylamine; mercury dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; 1.1: Grignard reaction / 5.1: Grignard reaction;
DOI:10.1016/j.tet.2007.02.087