N-[(1,1-dimethylethoxy)carbonyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester

Base Information

• Chemical Name: N-[(1,1-dimethylethoxy)carbonyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester
• CAS No.: 885019-68-1
• Molecular Formula: C₃₂H₄₅NO₁₃
• Molecular Weight: 651.708
• Mol file: 885019-68-1.mol

Synonyms:

Chemical Property of N-[(1,1-dimethylethoxy)carbonyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(1,1-dimethylethoxy)carbonyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester

There total 6 articles about N-[(1,1-dimethylethoxy)carbonyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-phenylalanine 1,1-dimethylethyl 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:

2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester (885019-64-7) → N-[(1,1-dimethylethoxy)carbonyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester (885019-68-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / nBu₄NF*3H₂O / tetrahydrofuran / 22 h / 0 - 20 °C

2.1: 0.24 g / pyridine; DMAP / 20 °C

3.1: BH₃*THF / tetrahydrofuran / 4 h / 0 °C

3.2: NaOH; H₂O₂ / tetrahydrofuran; H₂O / 2.5 h / 0 - 20 °C

4.1: 0.215 g / pyridine; DMAP / 20 °C

With pyridine; dmap; borane-THF; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1002/ejoc.200500690

Reference yield:

N-[(1,1-dimethylethoxy)carbonyl]-4-(1,2-dideoxy-D-arabino-hexenopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester (885019-66-9) → N-[(1,1-dimethylethoxy)carbonyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester (885019-68-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 0.24 g / pyridine; DMAP / 20 °C

2.1: BH₃*THF / tetrahydrofuran / 4 h / 0 °C

2.2: NaOH; H₂O₂ / tetrahydrofuran; H₂O / 2.5 h / 0 - 20 °C

3.1: 0.215 g / pyridine; DMAP / 20 °C

With pyridine; dmap; borane-THF; In tetrahydrofuran;

DOI:10.1002/ejoc.200500690

Reference yield:

N-[(1,1-dimethylethoxy)carbonyl]-4-(3,4,6-tri-O-acetyl-1,2-dideoxy-D-arabino-hexenopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester (885019-67-0) → N-[(1,1-dimethylethoxy)carbonyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester (885019-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BH₃*THF / tetrahydrofuran / 4 h / 0 °C

1.2: NaOH; H₂O₂ / tetrahydrofuran; H₂O / 2.5 h / 0 - 20 °C

2.1: 0.215 g / pyridine; DMAP / 20 °C

With pyridine; dmap; borane-THF; In tetrahydrofuran;

DOI:10.1002/ejoc.200500690

upstream raw materials:

acetic anhydride

N-[(1,1-dimethylethoxy)carbonyl]-4-(1,2-dideoxy-D-arabino-hexenopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester

N-[(1,1-dimethylethoxy)carbonyl]-4-(3,4,6-tri-O-acetyl-1,2-dideoxy-D-arabino-hexenopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester

2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester