tert-butyl (2R,3S,4R)-3,4-dihydroxy-2-[(2S,3S)-1,2,3-trihydroxy-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2R,3S,4R)-3,4-dihydroxy-2-[(2S,3S)-1,2,3-trihydroxy-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate
• CAS No.: 691905-81-4
• Molecular Formula: C₃₂H₃₉NO₈
• Molecular Weight: 565.664
• Mol file: 691905-81-4.mol

Synonyms:tert-butyl (2R,3S,4R)-3,4-dihydroxy-2-[(2S,3S)-1,2,3-trihydroxy-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate

Chemical Property of tert-butyl (2R,3S,4R)-3,4-dihydroxy-2-[(2S,3S)-1,2,3-trihydroxy-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,3S,4R)-3,4-dihydroxy-2-[(2S,3S)-1,2,3-trihydroxy-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate

There total 6 articles about tert-butyl (2R,3S,4R)-3,4-dihydroxy-2-[(2S,3S)-1,2,3-trihydroxy-4-(triphenylmethyloxy)butyl]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: 88.0%

tert-butyl (2R)-2-[(2S,3S)-4-(triphenylmethyloxy)-1,2,3-trihydroxybutyl]-2,5-dihydro-1H-pyrrole-1-carboxylate (691905-80-3) → tert-butyl (2R,3S,4R)-3,4-dihydroxy-2-[(2S,3S)-1,2,3-trihydroxy-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate (691905-81-4)

Guidance literature:

With 4-methylmorpholine N-oxide; potassium osmate(VI); In water; acetone; at 20 ℃; for 30h;

DOI:10.1021/jo049806y

Reference yield:

L-xylose (609-06-3) → tert-butyl (2R,3S,4R)-3,4-dihydroxy-2-[(2S,3S)-1,2,3-trihydroxy-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate (691905-81-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / ethanol / 16 h / 20 °C

2: 51 percent / triethylamine / acetonitrile; dimethylformamide / 19 h / 0 - 20 °C

3: 68 percent / pyridine / 18 h / 20 °C

4: 86 percent / (benzylidene)bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 18 h / Heating

5: 88 percent / N-methylmorpholine N-oxide / potassium osmate dihydrate / acetone; H₂O / 30 h / 20 °C

With pyridine; 4-methylmorpholine N-oxide; triethylamine; potassium osmate(VI); Grubbs catalyst first generation; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 1: Petasis reaction;

DOI:10.1021/jo049806y

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (2R,3S,4R)-3,4-dihydroxy-2-[(2S,3S)-1,2,3-trihydroxy-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate (691905-81-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 51 percent / triethylamine / acetonitrile; dimethylformamide / 19 h / 0 - 20 °C

2: 68 percent / pyridine / 18 h / 20 °C

3: 86 percent / (benzylidene)bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 18 h / Heating

4: 88 percent / N-methylmorpholine N-oxide / potassium osmate dihydrate / acetone; H₂O / 30 h / 20 °C

With pyridine; 4-methylmorpholine N-oxide; triethylamine; potassium osmate(VI); Grubbs catalyst first generation; In dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo049806y

upstream raw materials:

tert-butyl (2R)-2-[(2S,3S)-4-(triphenylmethyloxy)-1,2,3-trihydroxybutyl]-2,5-dihydro-1H-pyrrole-1-carboxylate

L-xylose

di-tert-butyl dicarbonate

(6E)-5-(allylamino)-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol

Downstream raw materials:

tert-butyl (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(1R,2S,3S)-1,2,3-tris(benzyloxy)-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate