2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• CAS No.: 141564-18-3
• Molecular Formula: C₃₆H₃₇F₃O₆
• Molecular Weight: 622.681
• Mol file: 141564-18-3.mol

Synonyms:2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Chemical Property of 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

There total 6 articles about 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 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: 92.0%

(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran (194088-19-2) + 2,2,2-trifluoroethanol (75-89-8) → 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (141564-18-3)

Guidance literature:

With FeCl₃/C; In acetonitrile; at 60 ℃; for 7h; stereoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1055/s-0037-1611801

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + 2,2,2-trifluoroethanol (75-89-8) → 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (141564-18-3) + trifluoroethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (141564-17-2)

Guidance literature:

With tetrabutylammonium perchlorate; triphenylphosphine; In dichloromethane; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1248/cpb.46.939

Reference yield:

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl acetate (56822-48-1) + 2,2,2-trifluoroethanol (75-89-8) → 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (141564-18-3) + trifluoroethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (141564-17-2)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 20 ℃; for 2h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.carres.2009.06.004

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

2,2,2-trifluoroethanol

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl acetate

(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran