methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

Base Information

• Chemical Name: methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside
• CAS No.: 445397-84-2
• Molecular Formula: C₅₁H₆₂N₂O₁₇
• Molecular Weight: 975.056

Synonyms:methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

Chemical Property of methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

There total 34 articles about methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-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: 61.0%

methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-4-O-pivaloyl-β-D-galactopyranoside (445397-83-1) → methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (445397-84-2)

Guidance literature:

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

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

Reference yield:

4-methoxyphenyl 3-O-benzyl-α-L-idopyranoside → methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (445397-84-2)

Guidance literature:

Multi-step reaction with 15 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: 79 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.5 h / 0 °C

5.1: aq. AcOH / 100 °C

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

7.1: 3.80 g / dimethylformamide / 1 h / 50 °C

8.1: 91 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

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

9.2: 58 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

10.1: Me₃SiOTf / toluene; CH₂Cl₂ / 0.5 h

11.1: 1.11 g / thiourea / ethanol; pyridine / 0.5 h / 80 °C

12.1: 75 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.5 h / -15 °C

13.1: 88 percent / Bu₃SnH; AIBN / benzene / 2.5 h / 20 - 80 °C

14.1: LiOH; aq. H₂O₂ / tetrahydrofuran / 16 h / 0 - 20 °C

15.1: 373 mg / aq. NaOH / methanol / 5 h / 20 °C

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

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

Reference yield:

4-methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-α-L-idopyranoside (445397-58-0) → methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (445397-84-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

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

2.2: 54 percent / DBU / CH₂Cl₂ / 1 h / 0 - 20 °C

3.1: 79 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.5 h / 0 °C

4.1: aq. AcOH / 100 °C

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

6.1: 3.80 g / dimethylformamide / 1 h / 50 °C

7.1: 91 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

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

8.2: 58 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

9.1: Me₃SiOTf / toluene; CH₂Cl₂ / 0.5 h

10.1: 1.11 g / thiourea / ethanol; pyridine / 0.5 h / 80 °C

11.1: 75 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.5 h / -15 °C

12.1: 88 percent / Bu₃SnH; AIBN / benzene / 2.5 h / 20 - 80 °C

13.1: LiOH; aq. H₂O₂ / tetrahydrofuran / 16 h / 0 - 20 °C

14.1: 373 mg / aq. NaOH / methanol / 5 h / 20 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hydroxide; calcium hypochlorite; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; acetic acid; thiourea; potassium bromide; In tetrahydrofuran; 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-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-4-O-pivaloyl-β-D-galactopyranoside

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 6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

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