Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Base Information

Chemical Name:Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside
CAS No.:303127-99-3
Molecular Formula:C₅₀H₆₀Cl₃NO₁₃Si
Molecular Weight:1017.47
Hs Code.:

Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Synonyms:Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

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Chemical Property of Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

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Technology Process of Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

There total 17 articles about Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-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: 68.0%

: 303127-95-9
Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

: 303127-85-7
Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano

: 303127-99-3
Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; toluene; at 20 ℃; for 0.5h;
DOI:10.1039/b002835p

Reference yield:

: 56644-73-6
Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

: 303127-99-3
Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: methanol / 16 h / 20 °C

2.1: 4.16 g / pyridine / CH₂Cl₂ / 1.3 h / 0 °C

3.1: pyridine / CH₂Cl₂ / 2 h / -15 - 0 °C

4.1: 3.33 g / NaNO₂ / dimethylformamide / 1.5 h / 20 °C

5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

5.2: 80 percent / TBAI / tetrahydrofuran / 5 h / 0 - 20 °C

6.1: methanol

7.1: 3 g / imidazole / dimethylformamide / 0.67 h / 0 °C

8.1: 68 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 0.5 h / 20 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; sodium nitrite; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Deacetylation / 2.1: Acylation / 3.1: Substitution / 4.1: Substitution / 5.1: Metallation / 5.2: Etherification / 6.1: Substitution / 7.1: Substitution / 8.1: Substitution;
DOI:10.1039/b002835p

Reference yield:

: 39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9
1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

: 303127-99-3
Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1.1: 69 percent / trimethylsilyl triflate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

2.1: 89 percent / methanol / 16 h / 20 °C

3.1: 84 percent / CF₃CO₂H / 0.33 h

4.1: 83 percent / pyridine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

5.1: 64 percent / AlCl₃; borane-trimethylamine complex; 4 Angstroem molecular sieves / diethyl ether; CH₂Cl₂ / 2 h / 0 °C

6.1: 79 percent / CrO₃; H₂SO₄ / acetone / 1 h / 20 °C

7.1: 1.56 g / DMAP; Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

8.1: cerium(IV) ammonium nitrite / H₂O; acetonitrile; toluene / 0.33 h / 20 °C

8.2: 71 percent / DBU / CH₂Cl₂ / 0.17 h / 0 °C

9.1: 68 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 0.5 h / 20 °C

With pyridine; chromium(VI) oxide; dmap; aluminium trichloride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; trimethylamine-borane; 4 A molecular sieve; sulfuric acid; triethylamine; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; water; acetone; toluene; acetonitrile; 1.1: Etherification / 2.1: Deacetylation / 3.1: Cyclization / 4.1: Acylation / 5.1: Ring cleavage / 6.1: Oxidation / 7.1: Acylation / 8.1: Substitution / 8.2: Addition / 9.1: Substitution;
DOI:10.1039/b002835p