methyl 3-O-(chloroacetyl)-4-O-benzyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 3-O-(chloroacetyl)-4-O-benzyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside
CAS No.:114828-00-1
Molecular Formula:C₃₃H₃₉Cl₃O₁₂
Molecular Weight:734.024
Hs Code.:

Synonyms:methyl 3-O-(chloroacetyl)-4-O-benzyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside

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Chemical Property of methyl 3-O-(chloroacetyl)-4-O-benzyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside

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Technology Process of methyl 3-O-(chloroacetyl)-4-O-benzyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside

There total 11 articles about methyl 3-O-(chloroacetyl)-4-O-benzyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside 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: 73.0%

: 131589-95-2
methyl 4-O-benzyl-6-deoxy-2-O-(3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside

: 541-88-8
Chloroacetic anhydride

: 114828-00-1
methyl 3-O-(chloroacetyl)-4-O-benzyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: With dmap; In pyridine; at 0 ℃; for 2.5h;

Reference yield:

: 3162-96-7
methyl 4,6-O-benzylidene-α-D-glucopyranoside

: 114828-00-1
methyl 3-O-(chloroacetyl)-4-O-benzyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / pyridine / Ambient temperature

2: 70 percent / BH₃*NMe₃, AlCl₃ / CH₂Cl₂

3: 82 percent / PPh₃, CBr₄ / tetrahydrofuran / 0.5 h / Ambient temperature

4: 84 percent / n-Bu₃SnH, azobisisobutyronitrile (AIBN) / benzene / 2 h / Heating

5: 84 percent / 1 M NaOMe / methanol / 2 h / Ambient temperature; pH 10

6: Hg(CN)2, Drierite / nitromethane; benzene / 1 h / 55 °C

7: 97 percent / 1 M NaOMe / methanol / Ambient temperature; pH 9

8: 73 percent / 4-(dimethylamino)pyridine (DMAP) / pyridine / 2.5 h / 0 °C

With pyridine; dmap; calcium sulfate; aluminium trichloride; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; trimethylamine-borane; tri-n-butyl-tin hydride; sodium methylate; mercury(II) cyanide; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; nitromethane; dichloromethane; benzene;

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 114828-00-1
methyl 3-O-(chloroacetyl)-4-O-benzyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: 93 percent / p-TsOH / dimethylformamide / 55 °C

2: 95 percent / pyridine / Ambient temperature

3: 70 percent / BH₃*NMe₃, AlCl₃ / CH₂Cl₂

4: 82 percent / PPh₃, CBr₄ / tetrahydrofuran / 0.5 h / Ambient temperature

5: 84 percent / n-Bu₃SnH, azobisisobutyronitrile (AIBN) / benzene / 2 h / Heating

6: 84 percent / 1 M NaOMe / methanol / 2 h / Ambient temperature; pH 10

7: Hg(CN)2, Drierite / nitromethane; benzene / 1 h / 55 °C

8: 97 percent / 1 M NaOMe / methanol / Ambient temperature; pH 9

9: 73 percent / 4-(dimethylamino)pyridine (DMAP) / pyridine / 2.5 h / 0 °C

With pyridine; dmap; calcium sulfate; aluminium trichloride; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; trimethylamine-borane; tri-n-butyl-tin hydride; sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; nitromethane; dichloromethane; N,N-dimethyl-formamide; benzene;