2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-tetrahydro-pyran-4-yl ester
• CAS No.: 202932-48-7
• Molecular Formula: C₃₅H₅₁NO₉
• Molecular Weight: 629.791
• Mol file: 202932-48-7.mol

Synonyms:2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-tetrahydro-pyran-4-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-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 (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-tetrahydro-pyran-4-yl ester

There total 1 articles about 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-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: 53.0%

(E)-3-phenylpropenal (14371-10-9) + tetra-O-pivaloyl-β-D-galactopyranosylamine (108342-87-6) → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-tetrahydro-pyran-4-yl ester (202932-48-7)

Guidance literature:

With acetic acid; In isopropyl alcohol; Ambient temperature;

DOI:10.1055/s-1999-2626

Reference yield:

1-(trimethylsiloxy)-1,3-butadiene (63383-46-0) + 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-tetrahydro-pyran-4-yl ester (202932-48-7) → (2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal (1438284-50-4) + (2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal (1438284-66-2)

Guidance literature:

With aluminum (III) chloride; In tetrahydrofuran; at -50 ℃; for 58h; Overall yield = 85 %; Overall yield = 178 mg; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2013.03.020

Reference yield:

allyltributylstanane (24850-33-7) + 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-tetrahydro-pyran-4-yl ester (202932-48-7) → N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-3(S)-amino-1(E)-phenyl-1,5-hexadiene + N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-3(R)-amino-1(E)-phenyl-1,5-hexadiene

Guidance literature:

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-tetrahydro-pyran-4-yl ester; With tin(IV) chloride; In tetrahydrofuran; at -78 ℃; for 2.5h;

allyltributylstanane; In tetrahydrofuran; at -78 - 20 ℃; Title compound not separated from byproducts;

DOI:10.1135/cccc20000816

upstream raw materials:

(E)-3-phenylpropenal

tetra-O-pivaloyl-β-D-galactopyranosylamine

Downstream raw materials:

(2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal

(2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal