N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-phenylalanine-N'-tert-butyl-amide

Base Information

• Chemical Name: N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-phenylalanine-N'-tert-butyl-amide
• CAS No.: 112022-94-3
• Molecular Formula: C₄₀H₆₂N₂O₁₁
• Molecular Weight: 746.939
• Mol file: 112022-94-3.mol

Synonyms:N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-phenylalanine-N'-tert-butyl-amide

Chemical Property of N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-phenylalanine-N'-tert-butyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-phenylalanine-N'-tert-butyl-amide

There total 4 articles about N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-phenylalanine-N'-tert-butyl-amide 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: 80.0%

formic acid (64-18-6) + tert-butyl isocyanide (630-18-2) + phenylacetaldehyde (122-78-1) + N-[2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl]amine (108342-87-6,120029-97-2,120030-03-7) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (112022-94-3) + 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((S)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (112022-94-3)

Guidance literature:

With zinc chloride diethyl ether; In tetrahydrofuran; at -25 ℃; for 72h;

DOI:10.1021/ja00210a084

Reference yield: 80.0%

formic acid (64-18-6) + tert-butyl isocyanide (630-18-2) + phenylacetaldehyde (122-78-1) + N-[2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl]amine (108342-87-6,120029-97-2,120030-03-7) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (112022-94-3) + 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((S)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (112022-94-3)

Guidance literature:

With zinc chloride diethyl ether; In tetrahydrofuran; at -25 ℃; for 72h;

DOI:10.1021/ja00210a084

Reference yield: 80.0%

formic acid (64-18-6) + tert-butylisonitrile (119072-55-8,7188-38-7) + phenylacetaldehyde (122-78-1) + tetra-O-pivaloyl-β-D-galactopyranosylamine (108342-87-6) → N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(R)-phenylalanine-N'-tert-butyl-amide (112022-94-3) + N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-phenylalanine-N'-tert-butyl-amide (112022-94-3)

Guidance literature:

With zinc chloride diethyl ether; In tetrahydrofuran; dichloromethane; at -25 ℃; for 24h; Yields of byproduct given;

DOI:10.1016/S0040-4020(01)86054-3

upstream raw materials:

formic acid

tert-butylisonitrile

phenylacetaldehyde

tetra-O-pivaloyl-β-D-galactopyranosylamine

Downstream raw materials:

D-(R)-phenylalanine

2,3,4,6-Tetra-O-pivaloyl-α/β-D-galactopyranose

(R)-2-Amino-N-tert-butyl-3-phenyl-propionamide; hydrochloride