2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-2-((S)-1-cyano-2,2-dimethyl-propylamino)-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-2-((S)-1-cyano-2,2-dimethyl-propylamino)-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester
• CAS No.: 133646-15-8
• Molecular Formula: C₃₂H₅₄N₂O₉
• Molecular Weight: 610.789
• Mol file: 133646-15-8.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-2-((S)-1-cyano-2,2-dimethyl-propylamino)-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-2-((S)-1-cyano-2,2-dimethyl-propylamino)-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester

There total 4 articles about 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-2-((S)-1-cyano-2,2-dimethyl-propylamino)-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl 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: 10.0%

trimethylsilyl cyanide (7677-24-9) + N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)neopentylideneamine (120255-26-7) → N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-D-tert-leucinonitrile (108342-92-3) + 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-((S)-1-cyano-2,2-dimethyl-propylamino)-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester (120030-00-4) + 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-2-((S)-1-cyano-2,2-dimethyl-propylamino)-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester (108342-92-3,120030-00-4,133646-15-8)

Guidance literature:

With zinc(II) chloride; In chloroform; at 20 ℃; for 2h; Yield given;

DOI:10.1016/S0040-4039(00)80504-3

Reference yield:

1,2,3,4,6-penta-O-pivaloyl-β-D-galactopyranose (108342-85-4,118711-42-5,220017-47-0) → N-(2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranosyl)-D-tert-leucinonitrile (133646-15-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / trimethylsilyl azide, SnCl₄ / CH₂Cl₂ / 5 h

2: 87 percent / H₂ / Raney nickel / methanol / 3 h / 760 Torr

3: propan-2-ol; acetic acid / 672 h / Ambient temperature

With trimethylsilylazide; hydrogen; tin(IV) chloride; nickel; In methanol; dichloromethane; acetic acid; isopropyl alcohol;

Reference yield:

2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl azide (108342-86-5) → N-(2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranosyl)-D-tert-leucinonitrile (133646-15-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / H₂ / Raney nickel / methanol / 3 h / 760 Torr

2: propan-2-ol; acetic acid / 672 h / Ambient temperature

With hydrogen; nickel; In methanol; acetic acid; isopropyl alcohol;

upstream raw materials:

sodium cyanide

tetra-O-pivaloyl-β-D-galactopyranosylamine

pivalaldehyde

1,2,3,4,6-penta-O-pivaloyl-β-D-galactopyranose