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

Base Information

• Chemical Name: methyl (2,3,4-tri-O-benzyl-6-O-picoloyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 1415590-77-0
• Molecular Formula: C₆₁H₆₃NO₁₂
• Molecular Weight: 1002.17
• Mol file: 1415590-77-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about methyl (2,3,4-tri-O-benzyl-6-O-picoloyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-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:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + ethyl 2,3,4-tri-O-benzyl-6-O-picolinyl-1-thio-β-D-glucopyranoside (1415590-58-7) → methyl O-(2,3,4-tri-O-benzyl-6-O-picoloyl-β-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (1415590-78-1) + methyl (2,3,4-tri-O-benzyl-6-O-picoloyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (1415590-77-0)

Guidance literature:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside; ethyl 2,3,4-tri-O-benzyl-6-O-picolinyl-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 2.5h; Optical yield = 39.394 %de;

DOI:10.1021/ja307355n

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + phenyl 2,3,4-tri-O-benzyl-6-O-picoloyl-1-thio-β-D-glucopyranoside → methyl O-(2,3,4-tri-O-benzyl-6-O-picoloyl-β-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (1415590-78-1) + methyl (2,3,4-tri-O-benzyl-6-O-picoloyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (1415590-77-0)

Guidance literature:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside; phenyl 2,3,4-tri-O-benzyl-6-O-picoloyl-1-thio-β-D-glucopyranoside; With palladium(II) bromide; In dichloromethane; at 20 ℃; for 3h; Molecular sieve; Inert atmosphere;

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; at -30 - 20 ℃; for 8h; Inert atmosphere;

With dmap; In dichloromethane; at 20 ℃; for 0.5h; Reagent/catalyst; Overall yield = 84 %; Overall yield = 31.2 mg; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02110

Reference yield:

2-Picolinic acid (98-98-6) + phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (87470-73-3,120403-26-1,38184-12-2) → methyl O-(2,3,4-tri-O-benzyl-6-O-picoloyl-β-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (1415590-78-1) + methyl (2,3,4-tri-O-benzyl-6-O-picoloyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (1415590-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

2.1: palladium(II) bromide / dichloromethane / 3 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 8 h / -30 - 20 °C / Inert atmosphere

2.3: 0.5 h / 20 °C / Inert atmosphere

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium(II) bromide; In dichloromethane;

DOI:10.1021/acs.orglett.5b02110

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

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

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

2-Picolinic acid