N-acetyl 4-C-(3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-D-talooctityl)-DL-phenylalanine methyl ester

Base Information

• Chemical Name: N-acetyl 4-C-(3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-D-talooctityl)-DL-phenylalanine methyl ester
• CAS No.: 219826-20-7
• Molecular Formula: C₂₈H₃₃NO₁₂
• Molecular Weight: 575.57
• Mol file: 219826-20-7.mol

Synonyms:N-acetyl 4-C-(3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-D-talooctityl)-DL-phenylalanine methyl ester

Chemical Property of N-acetyl 4-C-(3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-D-talooctityl)-DL-phenylalanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-acetyl 4-C-(3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-D-talooctityl)-DL-phenylalanine methyl ester

There total 2 articles about N-acetyl 4-C-(3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-D-talooctityl)-DL-phenylalanine methyl ester 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:

3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol (219864-05-8) → N-acetyl 4-C-(3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-D-talooctityl)-DL-phenylalanine methyl ester (219826-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / TMSOTf / 30 h / Ambient temperature

2: 1.) (Ph₃P)4Pd, CuI, piperidine, 2.) pyridine / 1) 80 deg C, 1 h; 2) overnight, rt

With piperidine; pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate;

DOI:10.1021/jo980517h

Reference yield:

acetic anhydride (108-24-7) + N-acetyl-4-iodo-(DL)-phenylalanine methyl ester (105089-61-0) + 3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-talooctitol (219826-07-0) → N-acetyl 4-C-(3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-D-talooctityl)-DL-phenylalanine methyl ester (219826-20-7)

Guidance literature:

With piperidine; pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Yield given; Multistep reaction; 1) 80 deg C, 1 h; 2) overnight, rt;

DOI:10.1021/jo980517h

Reference yield: 98.0%

N-acetyl 4-C-(3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-D-talooctityl)-DL-phenylalanine methyl ester (219826-20-7) → N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-talooctityl)-DL-phenylalanine

Guidance literature:

With methanol; sodium; for 2h; Ambient temperature;

DOI:10.1021/jo980517h

upstream raw materials:

acetic anhydride

N-acetyl-4-iodo-(DL)-phenylalanine methyl ester

3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-talooctitol

3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-talooctitol