benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-galactopyranoside

Base Information

Chemical Name:benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-galactopyranoside
CAS No.:101973-56-2
Molecular Formula:C₅₀H₅₅N₃O₁₀
Molecular Weight:858.001
Hs Code.:

Synonyms:benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-galactopyranoside

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Chemical Property of benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-galactopyranoside

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Technology Process of benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-galactopyranoside

There total 12 articles about benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-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:

: 100-51-6,185532-71-2
benzyl alcohol

: 101973-56-2
benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) Na, / 2.) toluene, RT; 30 min,

2: 78 percent / toluene-p-sulphonic acid, / dimethylformamide / 1.5 h / 60 °C

3: 1.) NaH, / 1.) DMF, 0 deg C, 1.5 h, 2.) DMF, RT; 1.5 h, 3.) MeOH, DMF, RT; 4 h,

4: 1.) 60percent acetic acid, 2.) NaH, / 1.) 100 deg C, 10 min, 2.) DMF, 0 deg C, 1 h, 3.) DMF, RT; 2 h,

5: 84 percent / 2,3-dichloro-5,6-dicyanobenzoquinone, / CH₂Cl₂; H₂O / 3 h / Ambient temperature

6: 1.) molecular sieves 4A, 2.) trimethylsilyl-trifluoromethanesulphonate / 1.) CH₂Cl₂, RT; 1 h, 2.) CH₂Cl₂, 3 h,

7: 1.) NaOMe, 2.) toluene-p-sulphonic acid, / 1.) MeOH, RT; overnight, 2.) RT; 7 h,

8: 1.) NaH, / 1.) DMF, 0 deg C, 1 h, 2.) DMF, RT; 5 h,

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium; sodium hydride; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)90139-3

Reference yield:

: 67673-39-6
3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide

: 101973-56-2
benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) Ag₂O, molecular sieves 4A, 3.) NaOMe, / 1.) toluene, 0 deg C, 2 h, 2.) toluene, RT; overnight, 3.) MeOH, RT; overnight,

2: 78 percent / toluene-p-sulphonic acid, / dimethylformamide / 1.5 h / 60 °C

3: 1.) NaH, / 1.) DMF, 0 deg C, 1.5 h, 2.) DMF, RT; 1.5 h, 3.) MeOH, DMF, RT; 4 h,

4: 1.) 60percent acetic acid, 2.) NaH, / 1.) 100 deg C, 10 min, 2.) DMF, 0 deg C, 1 h, 3.) DMF, RT; 2 h,

5: 84 percent / 2,3-dichloro-5,6-dicyanobenzoquinone, / CH₂Cl₂; H₂O / 3 h / Ambient temperature

6: 1.) molecular sieves 4A, 2.) trimethylsilyl-trifluoromethanesulphonate / 1.) CH₂Cl₂, RT; 1 h, 2.) CH₂Cl₂, 3 h,

7: 1.) NaOMe, 2.) toluene-p-sulphonic acid, / 1.) MeOH, RT; overnight, 2.) RT; 7 h,

8: 1.) NaH, / 1.) DMF, 0 deg C, 1 h, 2.) DMF, RT; 5 h,

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)90139-3

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 101973-56-2
benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 78 percent / toluene-p-sulphonic acid, / dimethylformamide / 1.5 h / 60 °C

2: 1.) NaH, / 1.) DMF, 0 deg C, 1.5 h, 2.) DMF, RT; 1.5 h, 3.) MeOH, DMF, RT; 4 h,

3: 1.) 60percent acetic acid, 2.) NaH, / 1.) 100 deg C, 10 min, 2.) DMF, 0 deg C, 1 h, 3.) DMF, RT; 2 h,

4: 84 percent / 2,3-dichloro-5,6-dicyanobenzoquinone, / CH₂Cl₂; H₂O / 3 h / Ambient temperature

5: 1.) molecular sieves 4A, 2.) trimethylsilyl-trifluoromethanesulphonate / 1.) CH₂Cl₂, RT; 1 h, 2.) CH₂Cl₂, 3 h,

6: 1.) NaOMe, 2.) toluene-p-sulphonic acid, / 1.) MeOH, RT; overnight, 2.) RT; 7 h,

7: 1.) NaH, / 1.) DMF, 0 deg C, 1 h, 2.) DMF, RT; 5 h,

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)90139-3