ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside
• CAS No.: 1415590-57-6
• Molecular Formula: C₃₅H₃₇NO₆S
• Molecular Weight: 599.748
• Mol file: 1415590-57-6.mol

Synonyms:ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside

There total 1 articles about ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-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: 89.0%

2-Picolinic acid (98-98-6) + ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (141263-02-7) → ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside (1415590-57-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1021/ja307355n

Reference yield: 99.0%

ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside (1415590-57-6) → ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (141263-02-7)

Guidance literature:

With copper diacetate; In methanol; dichloromethane; at 20 ℃; for 1.5h; Reagent/catalyst; Solvent; chemoselective reaction; Catalytic behavior; Inert atmosphere;

DOI:10.1039/d0ob00803f

Reference yield: 94.0%

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol (35303-86-7) + ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside (1415590-57-6) → methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside (1415590-89-4)

Guidance literature:

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol; ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside; In 1,2-dichloro-ethane; for 1h; Molecular sieve; Inert atmosphere;

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In 1,2-dichloro-ethane; at -30 - 42 ℃; for 7h;

DOI:10.1021/ja307355n

upstream raw materials:

2-Picolinic acid

ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl (2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl (2,3,6-tri-O-benzyl-4-O-picoloyl-β-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside

methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-β-D-glucopyranosyl)-α-D-glucopyranoside