2(R),5(R)-bis(methoxymethyl)-3(R),4(S)-dimethoxy-N-(benzyloxycarbonyl)pyrrolidine

Base Information

• Chemical Name: 2(R),5(R)-bis(methoxymethyl)-3(R),4(S)-dimethoxy-N-(benzyloxycarbonyl)pyrrolidine
• CAS No.: 191851-91-9
• Molecular Formula: C₁₈H₂₇NO₆
• Molecular Weight: 353.415
• Mol file: 191851-91-9.mol

Synonyms:2(R),5(R)-bis(methoxymethyl)-3(R),4(S)-dimethoxy-N-(benzyloxycarbonyl)pyrrolidine

Chemical Property of 2(R),5(R)-bis(methoxymethyl)-3(R),4(S)-dimethoxy-N-(benzyloxycarbonyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(R),5(R)-bis(methoxymethyl)-3(R),4(S)-dimethoxy-N-(benzyloxycarbonyl)pyrrolidine

There total 1 articles about 2(R),5(R)-bis(methoxymethyl)-3(R),4(S)-dimethoxy-N-(benzyloxycarbonyl)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: 97.0%

2,5-anhydro-N-benzyloxycarbonyl-2,5-imino-D-glucitol (191851-89-5) + methyl iodide (74-88-4) → 2(R),5(R)-bis(methoxymethyl)-3(R),4(S)-dimethoxy-N-(benzyloxycarbonyl)pyrrolidine (191851-91-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 20h; Ambient temperature;

DOI:10.1021/ja00153a008

Reference yield:

2(R),5(R)-bis(methoxymethyl)-3(R),4(S)-dimethoxy-N-(benzyloxycarbonyl)pyrrolidine (191851-91-9) → N-<1-phenyl-2(S)-<(benzyloxycarbonyl)amino>-3(R)-hydroxybutan>-4-<2'(R),5'(R)-bis(methoxymethyl)-3'(R),4'(S)-dimethoxy>pyrrolidine

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd/C / methanol / 3 h

2: 42 percent / Et₃N / methanol / 32 h / Heating

With hydrogen; triethylamine; palladium on activated charcoal; In methanol;

DOI:10.1021/ja00153a008

Reference yield:

2(R),5(R)-bis(methoxymethyl)-3(R),4(S)-dimethoxy-N-(benzyloxycarbonyl)pyrrolidine (191851-91-9) → [(1S,2S)-1-Benzyl-3-((2S,3R,4R,5R)-3,4-dimethoxy-2,5-bis-methoxymethyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid benzyl ester (172696-29-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd/C / methanol / 3 h

2: 80 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl, 1-hydroxybenzotriazole, diisopropylethylamine / dimethylformamide; acetonitrile / 18 h

With hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00153a008

upstream raw materials:

2,5-anhydro-N-benzyloxycarbonyl-2,5-imino-D-glucitol

methyl iodide

Downstream raw materials:

[(1S,2S)-1-Benzyl-3-((2S,3R,4R,5R)-3,4-dimethoxy-2,5-bis-methoxymethyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid benzyl ester