(2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine

Base Information

• Chemical Name: (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine
• CAS No.: 253776-38-4
• Molecular Formula: C₂₉H₃₉NO₇S
• Molecular Weight: 545.697
• Mol file: 253776-38-4.mol

Synonyms:(2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine

Chemical Property of (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine

There total 2 articles about (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine 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:

(2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane (116611-45-1) + (2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate) (253776-34-0) → (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine (253776-38-4) + (2R,3R,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine (253776-39-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -70 ℃; for 1h;

DOI:10.1021/jo991052d

Reference yield:

(R)-3-benzyloxy-1,2-propanediol (56552-80-8) → (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine (253776-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine / CH₂Cl₂ / 0.33 h / -30 °C

2: n-BuLi / tetrahydrofuran / 1 h / -70 °C

With pyridine; n-butyllithium; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Cyclization;

DOI:10.1021/jo991052d

Reference yield: 85.0%

(2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine (253776-38-4) → (2R,3R,5S)-1-tert-butoxycarbonyl-2-hydroxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 50 ℃;

DOI:10.1021/jo991052d

upstream raw materials:

(2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane

(2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate)

(R)-3-benzyloxy-1,2-propanediol