methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside

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Chemical Name:methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside
CAS No.:796873-43-3
Molecular Formula:C₂₂H₃₁NO₁₂
Molecular Weight:501.488
Hs Code.:

Synonyms:methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside

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Chemical Property of methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside

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Technology Process of methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside

There total 13 articles about methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-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: 81.0%

: 796873-53-5
methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

: 796873-43-3
methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 12h;
DOI:10.1016/j.carres.2004.07.018

Reference yield:

: 104707-00-8
methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

: 796873-43-3
methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 12 steps

1: 74 percent / N-idosuccinimide; silver triflate / CH₂Cl₂

2: 100 percent / NaOMe / methanol; tetrahydrofuran / 48 h / 20 °C

3: KBr; 1,2,6,6-tetramethylpiperidine-1-oxide; NaOCl / aq. NaHCO₃; tetrahydrofuran / 0.5 h / 20 °C

4: dimethylformamide / 12 h

5: 1.68 percent / DMAP / dimethylformamide / 12 h / 20 °C

6: 100 percent / TFA / 12 h / 20 °C

7: 65 percent / benzylamine / diethyl ether / 1 h / 0 °C

8: 81 percent / K₂CO₃ / CH₂Cl₂ / 12 h / 20 °C

9: 54 percent / BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

10: NaBH₄; NiCl₂*6H₂O; B(OH)3 / ethanol / 0.5 h

11: 51.0 mg / pyridine / 12 h

12: 81 percent / LiOH / methanol; tetrahydrofuran; H₂O / 12 h / 20 °C

With pyridine; dmap; lithium hydroxide; sodium hypochlorite; sodium tetrahydroborate; N-iodo-succinimide; 1,2,6,6-tetramethylpiperidine-1-oxide; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; boric acid; potassium carbonate; benzylamine; trifluoroacetic acid; potassium bromide; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; sodium hydrogencarbonate; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2004.07.018

Reference yield:

: 55682-57-0
1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

: 796873-43-3
methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 12 steps

1: 74 percent / N-idosuccinimide; silver triflate / CH₂Cl₂

2: 100 percent / NaOMe / methanol; tetrahydrofuran / 48 h / 20 °C

3: KBr; 1,2,6,6-tetramethylpiperidine-1-oxide; NaOCl / aq. NaHCO₃; tetrahydrofuran / 0.5 h / 20 °C

4: dimethylformamide / 12 h

5: 1.68 percent / DMAP / dimethylformamide / 12 h / 20 °C

6: 100 percent / TFA / 12 h / 20 °C

7: 65 percent / benzylamine / diethyl ether / 1 h / 0 °C

8: 81 percent / K₂CO₃ / CH₂Cl₂ / 12 h / 20 °C

9: 54 percent / BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

10: NaBH₄; NiCl₂*6H₂O; B(OH)3 / ethanol / 0.5 h

11: 51.0 mg / pyridine / 12 h

12: 81 percent / LiOH / methanol; tetrahydrofuran; H₂O / 12 h / 20 °C

With pyridine; dmap; lithium hydroxide; sodium hypochlorite; sodium tetrahydroborate; N-iodo-succinimide; 1,2,6,6-tetramethylpiperidine-1-oxide; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; boric acid; potassium carbonate; benzylamine; trifluoroacetic acid; potassium bromide; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; sodium hydrogencarbonate; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2004.07.018