N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-α-amino-4-phenyl-3-butenoic acid-N'-tert-butyl-amide

Base Information

• Chemical Name: N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-α-amino-4-phenyl-3-butenoic acid-N'-tert-butyl-amide
• CAS No.: 112023-00-4
• Molecular Formula: C₄₁H₆₂N₂O₁₁
• Molecular Weight: 758.95
• Mol file: 112023-00-4.mol

Synonyms:N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-α-amino-4-phenyl-3-butenoic acid-N'-tert-butyl-amide

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

There total 4 articles about N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-α-amino-4-phenyl-3-butenoic acid-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: 75.0%

(E)-3-phenylpropenal (14371-10-9) + formic acid (64-18-6) + tert-butyl isocyanide (630-18-2) + 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-[((E)-(R)-1-tert-butylcarbamoyl-3-phenyl-allyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (112023-00-4) + 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((E)-(S)-1-tert-butylcarbamoyl-3-phenyl-allyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (112023-00-4)

Guidance literature:

With zinc chloride diethyl ether; In tetrahydrofuran; at -25 ℃; for 24h;

DOI:10.1021/ja00210a084

Reference yield: 75.0%

(E)-3-phenylpropenal (14371-10-9) + formic acid (64-18-6) + tert-butyl isocyanide (630-18-2) + 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-[((E)-(R)-1-tert-butylcarbamoyl-3-phenyl-allyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (112023-00-4) + 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((E)-(S)-1-tert-butylcarbamoyl-3-phenyl-allyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (112023-00-4)

Guidance literature:

With zinc chloride diethyl ether; In tetrahydrofuran; at -25 ℃; for 24h;

DOI:10.1021/ja00210a084

Reference yield: 75.0%

formic acid (64-18-6) + tert-butylisonitrile (119072-55-8,7188-38-7) + tetra-O-pivaloyl-β-D-galactopyranosylamine (108342-87-6) + 3-phenyl-propenal (104-55-2) → N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(R)-α-amino-4-phenyl-3-butenoic acid-N'-tert-butyl-amide (112023-00-4) + N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-α-amino-4-phenyl-3-butenoic acid-N'-tert-butyl-amide (112023-00-4)

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

tetra-O-pivaloyl-β-D-galactopyranosylamine

3-phenyl-propenal