2-(trimethylsilyl)ethyl [methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate]-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl [methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate]-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside
CAS No.:372518-30-4
Molecular Formula:C₅₄H₆₂O₁₄Si
Molecular Weight:963.163
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl [methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate]-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl [methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate]-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl [methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate]-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside

There total 10 articles about 2-(trimethylsilyl)ethyl [methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate]-(1->6)-2,3,4-tri-O-benzyl-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: 80.8%

: 372518-28-0
methyl (2,3-di-O-benzoyl-4-O-methyl-α-D-gucopyranosyl trichloroacetamidate)uronate

: [(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol

: 372518-30-4
2-(trimethylsilyl)ethyl [methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate]-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/S0008-6215(01)00148-3

Reference yield:

: 152771-01-2
2-(Trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranoside

: 372518-30-4
2-(trimethylsilyl)ethyl [methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate]-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: pyridine / 12 h / 70 °C

2: NaH / dimethylformamide / 4 h / 20 °C

3: AcOH (80 percent) / 10 h / 55 °C

4: K₂Cr₂O₇; H₂SO₄ / acetone / 1 h / 55 °C

5: HCl / 2 h / 20 °C

6: hydrogen / Pd/C (10 percent) / methanol; tetrahydrofuran / 3 h / 20 °C

7: pyridine / 10 h / 20 °C

8: CF₃COOH / CH₂Cl₂ / 1 h / 0 °C

9: DBU / CH₂Cl₂ / 2 h / 0 °C

10: 80.8 percent / TMSOTf / CH₂Cl₂ / 0 - 20 °C

With pyridine; hydrogenchloride; potassium dichromate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; hydrogen; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(01)00148-3

Reference yield:

: 372518-26-8
methyl [2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-O-methyl-β-D-glucopyranosid]uronate

: 372518-30-4
2-(trimethylsilyl)ethyl [methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate]-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: hydrogen / Pd/C (10 percent) / methanol; tetrahydrofuran / 3 h / 20 °C

2: pyridine / 10 h / 20 °C

3: CF₃COOH / CH₂Cl₂ / 1 h / 0 °C

4: DBU / CH₂Cl₂ / 2 h / 0 °C

5: 80.8 percent / TMSOTf / CH₂Cl₂ / 0 - 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0008-6215(01)00148-3