methyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

Base Information

Chemical Name:methyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate
CAS No.:428865-80-9
Molecular Formula:C₂₅H₂₃Cl₄NO₉
Molecular Weight:623.271
Hs Code.:

Synonyms:methyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

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Chemical Property of methyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

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Technology Process of methyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

There total 4 articles about methyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate 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: 70.0%

: 545-06-2
trichloroacetonitrile

: 428865-79-6
methyl (4-methoxyphenyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-β-D-glucopyranoside)uronate

: 428865-80-9
methyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

Guidance literature:: methyl (4-methoxyphenyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-β-D-glucopyranoside)uronate; With ammonium cerium(IV) nitrate; In water; toluene; acetonitrile; at 20 ℃; for 0.5h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.166667h; Further stages.;
DOI:10.1002/1099-0690(200203)2002:5<815::AID-EJOC815>3.0.CO;2-A

Reference yield:

: 428865-77-4
4-methoxyphenyl 2-O-benzyol-3-O-benzyl-β-D-glucopyranoside

: 428865-80-9
methyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

Guidance literature:: Multi-step reaction with 3 steps

1.1: calcium hypochlorite; NaHCO₃; KBr / Aliquat 336; TEMPO / CH₂Cl₂; H₂O / 0.25 h / 0 °C

1.2: 74 percent / dimethylformamide / 2 h / 50 °C

2.1: 84 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: CAN / acetonitrile; toluene; H₂O / 0.5 h / 20 °C

3.2: 70 percent / DBU / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; calcium hypochlorite; ammonium cerium(IV) nitrate; sodium hydrogencarbonate; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; Aliquat 336; In dichloromethane; water; toluene; acetonitrile;
DOI:10.1002/1099-0690(200203)2002:5<815::AID-EJOC815>3.0.CO;2-A

Reference yield:

: 4-methoxyphenyl 2-O-benzyol-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

: 428865-80-9
methyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / AcOH; water / 0.75 h / 100 °C

2.1: calcium hypochlorite; NaHCO₃; KBr / Aliquat 336; TEMPO / CH₂Cl₂; H₂O / 0.25 h / 0 °C

2.2: 74 percent / dimethylformamide / 2 h / 50 °C

3.1: 84 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4.1: CAN / acetonitrile; toluene; H₂O / 0.5 h / 20 °C

4.2: 70 percent / DBU / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; calcium hypochlorite; ammonium cerium(IV) nitrate; water; sodium hydrogencarbonate; acetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; Aliquat 336; In dichloromethane; water; toluene; acetonitrile;
DOI:10.1002/1099-0690(200203)2002:5<815::AID-EJOC815>3.0.CO;2-A