O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Base Information

• Chemical Name: O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• CAS No.: 218961-16-1
• Molecular Formula: C₄₈H₄₈N₄O₁₀
• Molecular Weight: 840.93
• Mol file: 218961-16-1.mol

Synonyms:O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Chemical Property of O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

There total 9 articles about O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 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: 73.0%

Methyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside (162600-17-1) + 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (218961-14-9) → O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (218961-16-1) + O-(2,3,4-tri-O-benzyl-β-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Guidance literature:

With 4 A molecular sieve; tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; at -10 - 20 ℃; for 17h;

DOI:10.1002/(sici)1521-3765(19981102)4:11<2182::aid-chem2182>3.0.co;2-u

Reference yield: 62.0%

3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (218961-14-9) + p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (211801-54-6,807361-40-6) → O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (218961-16-1)

Guidance literature:

With tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c02971

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (218961-16-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / trimethylsilylazide, TMSOTf / acetonitrile / 4 h / Ambient temperature

2: 94 percent / DL-camphorsulfonic acid / acetonitrile / 96 h / Ambient temperature

3: 72 percent / NaH / dimethylformamide / 19 h / 0 - 20 °C

4: 83 percent / DL-camphosulfonic acid / methanol / 0.5 h / 50 °C

5: 73 percent / CuBr₂, Bu₄NBr, molecular sieves 4 Angstroem / CH₂Cl₂; dimethylformamide / 17 h / -10 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; 4 A molecular sieve; camphor-10-sulfonic acid; (1S)-10-camphorsulfonic acid; tetrabutylammomium bromide; sodium hydride; copper(ll) bromide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/(sici)1521-3765(19981102)4:11<2182::aid-chem2182>3.0.co;2-u

upstream raw materials:

Methyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside

3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide