2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 219924-26-2
• Molecular Formula: C₄₈H₇₂N₂O₁₂Si
• Molecular Weight: 897.191
• Mol file: 219924-26-2.mol

Synonyms:2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

There total 5 articles about 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-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:

formic acid (64-18-6) + tetra-O-pivaloyl-β-D-galactopyranosylamine (108342-87-6) + benzaldehyde (100-52-7) + tert-butyl-[(2-isocyanophenyl)methoxy]dimethylsilane (219924-10-4) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(S)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester + 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (219924-26-2)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; at -78 ℃; for 72h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo982186e

Reference yield:

2-Aminobenzyl alcohol (5344-90-1) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (219924-26-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / sodium hydride / tetrahydrofuran / 0 - 20 °C

2: 95 percent / pyridine / tetrahydrofuran / Ambient temperature

3: 80 percent / DABCO, triphosgene / CH₂Cl₂ / 1 h / 0 °C

4: ZnCl₂ / tetrahydrofuran / 72 h / -78 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; bis(trichloromethyl) carbonate; sodium hydride; zinc(II) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo982186e

Reference yield:

2-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]phenylamine (68847-33-6) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (219924-26-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / pyridine / tetrahydrofuran / Ambient temperature

2: 80 percent / DABCO, triphosgene / CH₂Cl₂ / 1 h / 0 °C

3: ZnCl₂ / tetrahydrofuran / 72 h / -78 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; bis(trichloromethyl) carbonate; zinc(II) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo982186e

upstream raw materials:

formic acid

tetra-O-pivaloyl-β-D-galactopyranosylamine

benzaldehyde

tert-butyl-[(2-isocyanophenyl)methoxy]dimethylsilane

Downstream raw materials:

(R)-phenylglycine hydrochloride