t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

Base Information

Chemical Name:t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate
CAS No.:864070-73-5
Molecular Formula:C₃₃H₃₅NO₁₃
Molecular Weight:653.64
Hs Code.:

Synonyms:t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

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Chemical Property of t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

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Technology Process of t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

There total 10 articles about t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate 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: 100.0%

: 544703-53-9
t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate

: 864070-73-5
t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(03)00287-9

Reference yield:

: 81704-03-2
3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-α-D-galacto-pyranosyl bromide

: 864070-73-5
t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

Guidance literature:: Multi-step reaction with 5 steps

1: 58 percent / AgOTf / CH₂Cl₂

2: 100 percent / H₂ / Pd-C / methanol; ethyl acetate

3: 95 percent / imid.; DMAP / dimethylformamide

4: 41 percent / DDQ / dioxane

5: 100 percent / TBAF / tetrahydrofuran

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; hydrogen; silver trifluoromethanesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(03)00287-9

Reference yield:

: 128316-64-3,481072-37-1
(+/-)-methyl 3-p-benzyloxyphenyl-2-hydroxypropionate

: 864070-73-5
t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

Guidance literature:: Multi-step reaction with 9 steps

1: KOH / methanol; H₂O

2: 100 percent / pyr

3: 78 percent / DMAP; DCC / CH₂Cl₂

4: 98 percent / NaOMe / methanol

5: 58 percent / AgOTf / CH₂Cl₂

6: 100 percent / H₂ / Pd-C / methanol; ethyl acetate

7: 95 percent / imid.; DMAP / dimethylformamide

8: 41 percent / DDQ / dioxane

9: 100 percent / TBAF / tetrahydrofuran

With pyridine; 1H-imidazole; dmap; potassium hydroxide; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; silver trifluoromethanesulfonate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(03)00287-9