methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside

Base Information

• Chemical Name: methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside
• CAS No.: 88713-85-3
• Molecular Formula: C₂₈H₃₁N₃O₅
• Molecular Weight: 489.571
• Mol file: 88713-85-3.mol

Synonyms:methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside

Chemical Property of methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside

There total 9 articles about methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-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: 86.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside (88713-85-3)

Guidance literature:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 ℃; for 0.5h;

With sodium azide; In N,N-dimethyl-formamide;

DOI:10.1021/jo035290r

Reference yield: 76.2%

Methyl 2,3,6-tri-O-benzyl-4-O-(methanesulfonyl)-α-D-galactopyranoside (71454-40-5) → methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside (88713-85-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 130 ℃; for 20h;

DOI:10.1016/0008-6215(83)84016-6

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside (88713-85-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / PPTS / dimethylformamide

2.1: 95 percent / NaH; TBAI / tetrahydrofuran

3.1: 80 percent / NaBH₃CN; HCl / tetrahydrofuran

4.1: pyridine; Tf₂O / CH₂Cl₂ / 0.5 h / 0 °C

4.2: 86 percent / NaN₃ / dimethylformamide

With pyridine; hydrogenchloride; trifluoromethylsulfonic anhydride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo035290r

upstream raw materials:

Methyl 2,3,6-tri-O-benzyl-4-O-(methanesulfonyl)-α-D-galactopyranoside

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

benzaldehyde dimethyl acetal

methyl-alpha-D-glucopyranoside

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-deoxy-β-L-threo-hex-4-enopyranoside

4-azido-2,3,6-tri-O-benzyl-4-deoxy-D-galactono-1,5-lactone

1-C-(4-azido-2,3,6-tri-O-benzyl-1,4-dideoxy-α-D-galactopyranosyl)propene

2-C-(6-iodo-2,3-di-O-benzyl-4-azido-4,6-dideoxy-α-D-galactopyranosyl)acetone