benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside
CAS No.:80035-37-6
Molecular Formula:C₄₉H₅₁NO₁₆
Molecular Weight:909.941
Hs Code.:

Synonyms:benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

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Chemical Property of benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

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Technology Process of benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

There total 9 articles about benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 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: 72.0%

: 80035-36-5
benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside

: 4163-60-4
β-D-galactose peracetate

: 80035-37-6
benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -25 - 20 ℃;
DOI:10.1016/j.tetlet.2004.09.034

Reference yield: 71.0%

: 80035-36-5
benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside

: 3068-32-4
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

: 80035-37-6
benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

Guidance literature:: With 4 A molecular sieve; mercury dibromide; at 85 ℃; for 8h;
DOI:10.1016/S0008-6215(00)80526-1

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 80035-37-6
benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / SnCl₄ / CH₂Cl₂ / 4 h / 20 - 25 °C

2: 81 percent / concentrated HCl / H₂O; acetone / 3.25 h / 70 °C

3: p-toluenesulfonic acid / acetonitrile / 8 h / 20 - 25 °C

4: 1.) NaH / dimethylformamide / 1.) 15 min, 5 deg C; 2.) 16 h, 20 deg C

5: 70 percent acetic acid / H₂O / 1.5 h / 100 °C

6: 66 percent / 1.) (Bu₃Sn)2O / toluene / 2 h, 140 deg C; 4.5 d, 80-90 deg C

7: 71 percent / HgBr₂, molecular sieve 4 A / 8 h / 85 °C

With hydrogenchloride; 4 A molecular sieve; tin(IV) chloride; sodium hydride; toluene-4-sulfonic acid; acetic acid; bis(tri-n-butyltin)oxide; mercury dibromide; In dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0008-6215(00)80526-1