(2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-carboxypropyl>pyrrolidine

Base Information

• Chemical Name: (2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-carboxypropyl>pyrrolidine
• CAS No.: 107650-91-9
• Molecular Formula: C₃₁H₃₅NO₆
• Molecular Weight: 517.622
• Mol file: 107650-91-9.mol

Synonyms:(2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-carboxypropyl>pyrrolidine

Chemical Property of (2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-carboxypropyl>pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-carboxypropyl>pyrrolidine

There total 7 articles about (2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-carboxypropyl>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: 51.0%

(2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-(ethoxycarbonyl)propyl>pyrrolidine (107741-01-5) → (1S,2R,8S,8aR)-1,2,8-tris(benzyloxy)-octahydro-5-indolizinone (107741-02-6) + (2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-carboxypropyl>pyrrolidine (107650-91-9)

Guidance literature:

With potassium hydroxide; In ethanol; at 120 ℃; for 336h;

DOI:10.1246/bcsj.59.3885

Reference yield:

methyl 3-acetamido-2-O-acetyl-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside (2484-81-3) → (2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-carboxypropyl>pyrrolidine (107650-91-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) 50percent acetic acid / 1.) water, 30 min, reflux; 2.) pyridine, 0 degC, 18 h

2: 1.) sodium hydride; 2.) pyridine / 1.) DMF, 100 degC, 30 min; 2.) 12 h

4: 1.) mercury(II) chloride, calcium carbonate; 2.) sodium hydride / 1.) acetonitrile, water, 4 h; 2.) THF, ambient temperature, 3 h

5: 86 percent / H₂ / Raney nickel T-4 / ethanol / 5 h / 760 Torr

6: 51 percent / aq. KOH / ethanol / 336 h / 120 °C

With pyridine; potassium hydroxide; hydrogen; sodium hydride; acetic acid; calcium carbonate; mercury dichloride; Raney nickel T-4; In ethanol;

DOI:10.1246/bcsj.59.3885

Reference yield:

benzyl bromide (100-39-0) → (2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-carboxypropyl>pyrrolidine (107650-91-9)

Guidance literature:

Multi-step reaction with 4 steps

2: 1.) mercury(II) chloride, calcium carbonate; 2.) sodium hydride / 1.) acetonitrile, water, 4 h; 2.) THF, ambient temperature, 3 h

3: 86 percent / H₂ / Raney nickel T-4 / ethanol / 5 h / 760 Torr

4: 51 percent / aq. KOH / ethanol / 336 h / 120 °C

With potassium hydroxide; hydrogen; sodium hydride; calcium carbonate; mercury dichloride; Raney nickel T-4; In ethanol;

DOI:10.1246/bcsj.59.3885

upstream raw materials:

(2R,3S,4R)-1-acetyl-3,4-bis(benzyloxy)-2-<(1S)-1-benzyloxy-3-(ethoxycarbonyl)propyl>pyrrolidine

methyl 3-acetamido-2-O-acetyl-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

benzyl bromide

methyl 3-acetamido-2-O-acetyl-3-deoxy-6-O-tosyl-α-D-glucopyranoside

Downstream raw materials:

(1S,2R,8S,8aR)-1,2,8-tris(benzyloxy)-octahydro-5-indolizinone