benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS No.: 337975-50-5
• Molecular Formula: C₂₂H₃₅NO₆Si
• Molecular Weight: 437.608
• Mol file: 337975-50-5.mol

Synonyms:benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

Chemical Property of benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

There total 14 articles about benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate 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: 65.0%

benzyl chloroformate (501-53-1,94274-21-2) + Acetic acid (2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidin-3-yl ester → benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate (337975-50-5) + (2R,3S,5R)-3-Acetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(01)00071-5

Reference yield: 39.0%

(2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate (1450984-45-8) → benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate (337975-50-5)

Guidance literature:

(2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate; With mercury(II) diacetate; In acetonitrile; at 0 ℃; for 1.5h;

With sodium tetrahydroborate; oxygen; In N,N-dimethyl-formamide; for 3h;

DOI:10.1021/acsinfecdis.8b00105

Reference yield:

Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-3-oxiranyl-propyl]-carbamic acid benzyl ester → benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate (337975-50-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / pyridine; DMAP / 20 °C

2: H₂ / Pd/C / methanol / 20 °C

3: 65 percent / aq. NaHCO₃ / CH₂Cl₂ / 20 °C

With pyridine; dmap; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(01)00071-5

upstream raw materials:

benzyl chloroformate

Acetic acid (1S,2R)-2-(benzyl-benzyloxycarbonyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-oxiranylmethyl-propyl ester

N-(benzyloxycarbonyl)-D-serine

(R)-benzyl 3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropane-2-ylcarbamate

Downstream raw materials:

C₂₆H₃₆N₂O₉Si

benzyl (2R,3S,5S)-3-acetoxy-5-((dibenzyloxyphosphoryloxy)methyl)-2-((tert-butyldimethylsilyloxy)methyl)pyrrolidine-1-carboxylate

C₂₈H₃₂NO₈P

(5R,4S,2S)-4-hydroxy-5-((phenylmethoxy)methyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester