O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Base Information

Chemical Name:O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
CAS No.:188398-88-1
Molecular Formula:C₅₇H₅₆N₄O₁₂
Molecular Weight:989.091
Hs Code.:

Synonyms:O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

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Chemical Property of O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

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Technology Process of O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

There total 11 articles about O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-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: 41.0%

: 112289-36-8
2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl fluoride

: 161315-66-8
3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

: 188398-88-1
O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; a) 0 deg C, 1 h, b) RT, 3 h;
DOI:10.1016/0008-6215(93)84071-D

Reference yield:

: 3068-32-4
1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose

: 188398-88-1
O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-lutidine, Bu₄NBr / nitromethane / 20 h / 40 °C

2: 0.1 M NaOMe / methanol / 1 h / Ambient temperature

3: 80percent NaH / dimethylformamide / 15 h / Ambient temperature

4: 1.) conc. H₂SO₄, 2.) pyridine / 1.) 1,4-dioxane, reflux, 2 h, 2.) RT, 16 h

5: 68 percent / HF, pyridine / CH₂Cl₂ / 3 h / 0 °C

6: 41 percent / 4A molecular sieves, BF₃*OEt₂ / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 3 h

With pyridine; 2,6-dimethylpyridine; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; hydrogen fluoride; tetrabutylammomium bromide; sodium methylate; sodium hydride; In methanol; nitromethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(93)84071-D

Reference yield:

: 3254-15-7
3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose

: 188398-88-1
O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Guidance literature:: Multi-step reaction with 5 steps

1: 0.1 M NaOMe / methanol / 1 h / Ambient temperature

2: 80percent NaH / dimethylformamide / 15 h / Ambient temperature

3: 1.) conc. H₂SO₄, 2.) pyridine / 1.) 1,4-dioxane, reflux, 2 h, 2.) RT, 16 h

4: 68 percent / HF, pyridine / CH₂Cl₂ / 3 h / 0 °C

5: 41 percent / 4A molecular sieves, BF₃*OEt₂ / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 3 h

With pyridine; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; hydrogen fluoride; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(93)84071-D