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

Base Information

• Chemical Name: methyl 2-azido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside
• CAS No.: 128716-67-6
• Molecular Formula: C₂₇H₃₅N₃O₁₄
• Molecular Weight: 625.587
• Mol file: 128716-67-6.mol

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

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

There total 11 articles about methyl 2-azido-6-O-benzyl-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: 70.0%

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) → methyl 2-azido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside (128716-67-6)

Guidance literature:

With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃;

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

Reference yield: 16.0%

methyl 2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (109914-57-0) + methyl (2,3,4-tetra-O-acetyl-α-L-idopyranosyl bromide)uroate (108032-44-6) → methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (109914-58-1) + methyl 3-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside + methyl 2-azido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside (128716-67-6)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; Yield given. Title compound not separated from byproducts; -20 deg C --> -5 deg C, 1 h;

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

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → methyl 2-azido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-β-D-galactopyranoside (128716-67-6)

Guidance literature:

Multi-step reaction with 3 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

3: 70 percent / hydrogen chloride, sodium cyanoborohydride, activated molecular sieve (4 Angstroem) / diethyl ether; tetrahydrofuran / 0 °C

With hydrogenchloride; 4 A molecular sieve; 10-camphorsufonic acid; silver trifluoromethanesulfonate; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; nitromethane; dichloromethane;

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

upstream raw materials:

methyl 2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

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

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

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