methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside
• CAS No.: 128716-65-4
• Molecular Formula: C₂₇H₃₃N₃O₁₄
• Molecular Weight: 623.571
• Mol file: 128716-65-4.mol

Synonyms:methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside

Chemical Property of methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside

There total 6 articles about methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside 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: 68.0%

methyl 2-azido-2-deoxy-4,6-O-benzylidenbe-β-D-galacto-pyranoside (52885-40-2) + methyl (2,3,4-tri-O-acetyl-α-L-idopyranosyl trichloroacetimidate)uronate (128716-61-0) → methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside (128716-65-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -20 ℃; for 0.25h;

DOI:10.1016/0008-6215(89)85086-4

Reference yield: 54.0%

methyl 2-azido-2-deoxy-4,6-O-benzylidenbe-β-D-galacto-pyranoside (52885-40-2) + methyl (2,3,4-tetra-O-acetyl-α-L-idopyranosyl bromide)uroate (108032-44-6) → methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside (128716-65-4)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 2h; -15 deg C --> room temperature;

DOI:10.1016/0008-6215(89)85086-4

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside (128716-65-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / (+/-)-10-camphersulfonic acid / nitromethane / 1.5 h / 20 °C

2: 54 percent / silver triflate, activated molecular sieve (4 Angstroem) / CH₂Cl₂ / 2 h / -15 deg C --> room temperature

With 4 A molecular sieve; 10-camphorsufonic acid; silver trifluoromethanesulfonate; In nitromethane; dichloromethane;

DOI:10.1016/0008-6215(89)85086-4

upstream raw materials:

methyl 2-azido-2-deoxy-4,6-O-benzylidenbe-β-D-galacto-pyranoside

methyl (2,3,4-tetra-O-acetyl-α-L-idopyranosyl bromide)uroate

methyl (2,3,4-tri-O-acetyl-α-L-idopyranosyl trichloroacetimidate)uronate

benzaldehyde dimethyl acetal

Downstream raw materials:

methyl 2-acetamido-2-deoxy-3-O-(α-L-idopyranosyluronic acid)-4-O-sulfo-β-D-galactopyranoside, disodium salt

methyl 2-azido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside