(2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2Z)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine

Base Information

• Chemical Name: (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2Z)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine
• CAS No.: 90762-27-9
• Molecular Formula: C₃₃H₃₇NO₆
• Molecular Weight: 543.66
• Mol file: 90762-27-9.mol

Synonyms:(2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2Z)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine

Chemical Property of (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2Z)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2Z)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine

There total 27 articles about (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2Z)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>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: 75.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (S)-((2S,3S,4R)-1-Acetyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-benzyloxy-acetaldehyde (90706-24-4) → (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2Z)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine (90762-27-9) + (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2E)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine (90706-26-6)

Guidance literature:

With sodium hydride;

DOI:10.1246/cl.1984.513

Reference yield:

methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-α-D-mannopyranoside (72523-35-4) → (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2Z)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine (90762-27-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) 2M HCl; 2.) pyridine / 1.) reflux, 13 h; 2.) overnight

2: 1.) sodium methoxide / 1.) MeOH, 2 h; 2.) conc. HCl, -15 deg C, 7 h

3: 4-dimethylaminopyridine / pyridine / 3.5 h / 70 °C

4: 1.) sodium hydride / 1.) DMF, 20 min; 2.) DMF, overnight

5: toluene-p-sulfonic acid monohydrate / methanol / 2 h

6: 77 percent / pyridine / 16 h

7: 93 percent / aq. sodium hydroxide / dioxane / 0.5 h / Heating

8: mercury(II) chloride, calcium carbonate / H₂O; acetonitrile / 0.83 h

9: 2 percent / 60percent sodium hydride in mineral oil / tetrahydrofuran / 4 h

With pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; calcium carbonate; mercury dichloride; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; acetonitrile;

DOI:10.1016/0008-6215(85)85186-7

Reference yield:

methyl 3-acetamido-4,6-O-benzylidene-3-deoxy-2-O-mesyl-α-D-glucopyranoside (90706-18-6) → (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2Z)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine (90762-27-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 97 percent / 0.5percent aq. HCl / methanol / 1 h / Heating

2: 1.) sodium acetate; 2.) pyridine / 1.) water, 2-methoxyethanol, 25 h, reflux; 2.) 3 h

3: 1.) 2M HCl; 2.) pyridine / 1.) reflux, 13 h; 2.) overnight

4: 1.) sodium methoxide / 1.) MeOH, 2 h; 2.) conc. HCl, -15 deg C, 7 h

5: 4-dimethylaminopyridine / pyridine / 3.5 h / 70 °C

6: 1.) sodium hydride / 1.) DMF, 20 min; 2.) DMF, overnight

7: toluene-p-sulfonic acid monohydrate / methanol / 2 h

8: 77 percent / pyridine / 16 h

9: 93 percent / aq. sodium hydroxide / dioxane / 0.5 h / Heating

10: mercury(II) chloride, calcium carbonate / H₂O; acetonitrile / 0.83 h

11: 2 percent / 60percent sodium hydride in mineral oil / tetrahydrofuran / 4 h

With pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; calcium carbonate; mercury dichloride; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; acetonitrile;

DOI:10.1016/0008-6215(85)85186-7

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(S)-((2S,3S,4R)-1-Acetyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-benzyloxy-acetaldehyde

Methyl 3-acetamido-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-α-D-mannopyranoside

Downstream raw materials:

swainsonine

swainsonine tribenzylate

(1S,2R,8R,8aR)-1,2,8-tris(benzyloxy)hexahydroindolizin-5(1H)-one

(2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R)-1-benzyloxy-3-ethoxycarbonylpropyl>pyrrolidine