methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 174745-79-0
• Molecular Formula: C₄₈H₅₄O₉
• Molecular Weight: 774.951

Synonyms:methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Chemical Property:

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Technology Process of methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

There total 13 articles about methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(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: 77.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + C27H30O6S → methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (174745-79-0)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 - 20 ℃; for 18.25h; stereoselective reaction;

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + (4S,5S,6S)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol → methyl (3,4-di-O-benzyl-2,6-dideoxy-α-L-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (174745-80-3) + methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (174745-79-0)

Guidance literature:

(4S,5S,6S)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol; With 3,3-dichloro-1,2-diphenylcyclopropene; tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside; In dichloromethane; at 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol200726v

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + 2,6-dideoxy-3,4-di-O-benzyl-L-glucopyranosyl trichloroacetimidate → methyl (3,4-di-O-benzyl-2,6-dideoxy-α-L-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (174745-80-3) + methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (174745-79-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 2.5h; Overall yield = 71 mg; Inert atmosphere;

DOI:10.1039/c6ob00025h

upstream raw materials:

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

C₂₈H₃₁O₆^(1-)*K⁽¹⁺⁾

3,4-di-O-benzyl-L-rhamnal

benzyl bromide

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