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

Base Information

• Chemical Name: (3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one
• CAS No.: 944544-00-7
• Molecular Formula: C₃₁H₃₅NO₆
• Molecular Weight: 517.622
• Mol file: 944544-00-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one 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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one (158349-27-0) → (3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one (944544-00-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.tet.2007.02.087

Reference yield:

(3S,4R,5R)-5-benzyloxymethyl-3,4-dibenzyloxy-1-(4-methoxybenzyl)-pyrrolidin-2-one (944543-93-5) → (3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one (944544-00-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / ceric ammonium nitrate / acetonitrile; H₂O / 5.5 h / 0 - 20 °C

2: 95 percent / 4-(dimethylamino)pyridine; NEt₃ / CH₂Cl₂ / 4 h / 20 °C

With dmap; ammonium cerium(IV) nitrate; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.tet.2007.02.087

Reference yield:

(3S,4S)-1-(4-methoxybenzyl)-3,4-dibenzyloxy-2,5-pyrrolidinedione (944543-96-8) → (3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one (944544-00-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / magnesium; mercury(II) chloride / tetrahydrofuran / 7 h / 20 °C

2: 777 mg / triethylsilane; boron trifluoride etherate / CH₂Cl₂ / -78 - 20 °C

3: 85 percent / ceric ammonium nitrate / acetonitrile; H₂O / 5.5 h / 0 - 20 °C

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

With triethylsilane; dmap; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; magnesium; triethylamine; mercury dichloride; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1: Grignard reaction;

DOI:10.1016/j.tet.2007.02.087

upstream raw materials:

di-tert-butyl dicarbonate

(3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one

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

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

Downstream raw materials:

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

C₃₂H₃₉NO₆

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

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