methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

Base Information

• Chemical Name: methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside
• CAS No.: 1300080-67-4
• Molecular Formula: C₂₀H₂₅NO₇
• Molecular Weight: 391.421
• Mol file: 1300080-67-4.mol

Synonyms:methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

Chemical Property of methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

There total 1 articles about methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside 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: 67.0%

methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside (1291090-59-9) → methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside (1300080-67-4)

Guidance literature:

With trimethylamine-borane; boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 1.5h; Cooling with ice; Inert atmosphere;

DOI:10.1039/c1ob00021g

Reference yield: 86.5%

methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside (1300080-67-4) + 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) → methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

Guidance literature:

methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside; 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate; In dichloromethane; acetonitrile; at 20 ℃; for 0.666667h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -25 ℃; for 0.5h; Inert atmosphere;

With sodium hydrogencarbonate; In dichloromethane; acetonitrile; regioselective reaction; Inert atmosphere;

DOI:10.1039/c1ob00021g

Reference yield: 57.0%

methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside (1300080-67-4) + C38H66O7S2Si3 → methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside (1467030-42-7)

Guidance literature:

methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside; C₃₈H₆₆O₇S₂Si₃; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -50 ℃; for 0.916667h; regioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.carres.2013.08.002

upstream raw materials:

methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

Downstream raw materials:

methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

C₄₁H₄₉NO₁₆