[3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronic acid]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-methyl 3-O-benzyl-α-L-idopyranosiduronic acid

Base Information

• Chemical Name: [3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronic acid]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-methyl 3-O-benzyl-α-L-idopyranosiduronic acid
• CAS No.: 445397-75-1
• Molecular Formula: C₅₀H₅₉NO₁₉
• Molecular Weight: 978.014

Synonyms:[3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronic acid]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-methyl 3-O-benzyl-α-L-idopyranosiduronic acid

Chemical Property of [3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronic acid]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-methyl 3-O-benzyl-α-L-idopyranosiduronic acid

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

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Technology Process of [3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronic acid]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-methyl 3-O-benzyl-α-L-idopyranosiduronic acid

There total 20 articles about [3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronic acid]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-methyl 3-O-benzyl-α-L-idopyranosiduronic acid 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: 66.0%

methyl O-[methyl 2-O-benzoyl-3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-4-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate (445397-73-9) → [3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronic acid]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-methyl 3-O-benzyl-α-L-idopyranosiduronic acid (445397-75-1)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 96h;

DOI:10.1016/S0008-6215(02)00060-5

Reference yield:

1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-L-idopyranose (175978-71-9) → [3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronic acid]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-methyl 3-O-benzyl-α-L-idopyranosiduronic acid (445397-75-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 98 percent / trimethylsilyl triflate / CH₂Cl₂ / 1.5 h / 20 °C

2.1: NaOMe / methanol / 20 °C

3.1: 4.37 g / TFA / 3 h / 20 °C

4.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

5.1: ceric ammonium nitrate / toluene; acetonitrile; H₂O / 0.08 h / 20 °C

5.2: 54 percent / DBU / CH₂Cl₂ / 1 h / 0 - 20 °C

6.1: 78 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.5 h / 0 °C

7.1: 3.20 g / aq. AcOH / 100 °C

8.1: calcium hypochlorite; NaHCO₃; TEMPO / KBr / H₂O; CH₂Cl₂; acetonitrile / 0.75 h / 0 °C

9.1: 2.20 g / dimethylformamide / 1 h / 50 °C

10.1: 85 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

11.1: ceric ammonium nitrate / toluene; acetonitrile; H₂O / 0.25 h / 20 °C

11.2: 55 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

12.1: 61 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.5 h / -15 °C

13.1: thiourea / pyridine; ethanol / 0.5 h / 80 °C

14.1: 667 mg / Me₃SiOTf / CH₂Cl₂; toluene / 1 h / 20 °C

15.1: 92 percent / Bu₃SnH; AIBN / benzene / 2.5 h / 20 - 80 °C

16.1: 66 percent / aq. NaOH / methanol / 96 h / 20 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; calcium hypochlorite; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; sodium methylate; sodium hydrogencarbonate; acetic acid; thiourea; trifluoroacetic acid; potassium bromide; In pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 2.1: Zemplen reaction;

DOI:10.1016/S0008-6215(02)00060-5

Reference yield:

4-methoxyphenyl 3-O-benzyl-α-L-idopyranoside → [3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronic acid]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-methyl 3-O-benzyl-α-L-idopyranosiduronic acid (445397-75-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 4.37 g / TFA / 3 h / 20 °C

2.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: ceric ammonium nitrate / toluene; acetonitrile; H₂O / 0.08 h / 20 °C

3.2: 54 percent / DBU / CH₂Cl₂ / 1 h / 0 - 20 °C

4.1: 78 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.5 h / 0 °C

5.1: 3.20 g / aq. AcOH / 100 °C

6.1: calcium hypochlorite; NaHCO₃; TEMPO / KBr / H₂O; CH₂Cl₂; acetonitrile / 0.75 h / 0 °C

7.1: 2.20 g / dimethylformamide / 1 h / 50 °C

8.1: 85 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

9.1: ceric ammonium nitrate / toluene; acetonitrile; H₂O / 0.25 h / 20 °C

9.2: 55 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 61 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.5 h / -15 °C

11.1: thiourea / pyridine; ethanol / 0.5 h / 80 °C

12.1: 667 mg / Me₃SiOTf / CH₂Cl₂; toluene / 1 h / 20 °C

13.1: 92 percent / Bu₃SnH; AIBN / benzene / 2.5 h / 20 - 80 °C

14.1: 66 percent / aq. NaOH / methanol / 96 h / 20 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; calcium hypochlorite; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; sodium hydrogencarbonate; acetic acid; thiourea; trifluoroacetic acid; potassium bromide; In pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1016/S0008-6215(02)00060-5

upstream raw materials:

methyl O-[methyl 2-O-benzoyl-3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-4-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate

1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-L-idopyranose

4-methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-α-L-idopyranoside

4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-α-L-idopyranoside

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