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

Base Information

• Chemical Name: (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one
• CAS No.: 158349-27-0
• Molecular Formula: C₂₆H₂₇NO₄
• Molecular Weight: 417.505
• Mol file: 158349-27-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)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: 69.0%

(3S,4S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5-hydroxy-pyrrolidin-2-one → (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one (158349-27-0)

Guidance literature:

With sodium cyanoborohydride; In formic acid; acetonitrile; for 2h; Heating;

DOI:10.1016/S0040-4020(01)86715-6

Reference yield:

tri-O-benzyl-D-arabinolactone (14233-64-8) → (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one (158349-27-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / 8 M ammonia / methanol / 1.5 h

2: 88 percent / Dess Martin reagent / CH₂Cl₂ / 4 h / Ambient temperature

3: 94 percent / 8 M ammonia / methanol / 4 h

4: 69 percent / sodium cyanoborohydride / acetonitrile; formic acid / 2 h / Heating

With ammonium hydroxide; sodium cyanoborohydride; Dess-Martin periodane; In methanol; formic acid; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)86715-6

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one (158349-27-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / dimethyl sulfoxide, acetic anhydride / 12 h

2: 99 percent / 8 M ammonia / methanol / 1.5 h

3: 88 percent / Dess Martin reagent / CH₂Cl₂ / 4 h / Ambient temperature

4: 94 percent / 8 M ammonia / methanol / 4 h

5: 69 percent / sodium cyanoborohydride / acetonitrile; formic acid / 2 h / Heating

With ammonium hydroxide; acetic anhydride; sodium cyanoborohydride; Dess-Martin periodane; dimethyl sulfoxide; In methanol; formic acid; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)86715-6

upstream raw materials:

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

C₃₄H₃₅NO₆

Benzyloxymethyl chloride

(2S,3S)-diethyl 2,3-bis(phenylmethoxy)succinate

Downstream raw materials:

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

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

(5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-5,6,7,7a-tetrahydropyrrolizin-3-one

(2R,3R,4R,5R)-1-allyl-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-vinylpyrrolidine