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

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-α-D-glucopyranosyl fluoride
CAS No.:188398-90-5
Molecular Formula:C₅₇H₅₆FNO₁₂
Molecular Weight:966.07
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-α-D-glucopyranosyl fluoride

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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-α-D-glucopyranosyl fluoride

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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-α-D-glucopyranosyl fluoride

There total 14 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-α-D-glucopyranosyl fluoride 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:

: 188398-89-2
1-4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)>-4,5-di-tert-butyloxycarbonyl-1,2,3-triazole

: 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 fluoride

: 188398-90-5
O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl fluoride

Guidance literature:: With pyridine; hydrogen fluoride; In dichloromethane; at 0 ℃; for 16h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1016/0008-6215(93)84071-D

Reference yield:

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

: 188398-90-5
O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl fluoride

Guidance literature:: Multi-step reaction with 8 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

7: 68 percent / toluene / 72 h / 100 °C

8: HF, pyridine / CH₂Cl₂ / 16 h / 0 °C

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; toluene;
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

: 188398-90-5
O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl fluoride

Guidance literature:: Multi-step reaction with 7 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

6: 68 percent / toluene / 72 h / 100 °C

7: HF, pyridine / CH₂Cl₂ / 16 h / 0 °C

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; toluene;
DOI:10.1016/0008-6215(93)84071-D