methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-hydroxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate

Base Information

• Chemical Name: methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-hydroxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate
• CAS No.: 351530-34-2
• Molecular Formula: C₅₃H₆₃NO₁₆
• Molecular Weight: 970.08

Synonyms:methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-hydroxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate

Chemical Property of methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-hydroxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-hydroxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate

There total 11 articles about methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-hydroxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate 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: 95.0%

methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate (351530-31-9) → methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-hydroxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate (351530-34-2)

Guidance literature:

With hydrazinium monoacetate; In ethanol; toluene; for 3h;

DOI:10.1016/S0008-6215(01)00071-4

Reference yield:

8-bromooctanol (50816-19-8) → methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-hydroxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate (351530-34-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 53 percent / NaH / dimethylformamide / 5 h / -50 - 0 °C

2: 96 percent / DMAP / 1,2-dichloro-ethane; pyridine / 4 h

3: 80 percent / TBAF / tetrahydrofuran / 96 h

4: DMSO; (COCl)2; Et(i-Pr)2N / CH₂Cl₂ / 1.08 h

5: NaClO₂; 2-methyl-2-butene; NaHPO₄*2H₂O / 2-methyl-propan-2-ol

6: 1.498 g / toluene; methanol; hexane

7: H₂ / Lindlar catalyst / ethyl acetate

8: 23.6 mg / pyridine

9: 95 percent / H₂NNH₂*AcOH / ethanol; toluene / 3 h

With pyridine; dmap; sodium chlorite; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; hydrazinium monoacetate; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 4: Swern oxidation;

DOI:10.1016/S0008-6215(01)00071-4

Reference yield:

4-methoxyphenyl O-(2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl)-(1->4)-6-O-tert-butyldiphenylsilyl-2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranoside → methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-hydroxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate (351530-34-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 53 percent / NaH / dimethylformamide / 5 h / -50 - 0 °C

2: 96 percent / DMAP / 1,2-dichloro-ethane; pyridine / 4 h

3: 80 percent / TBAF / tetrahydrofuran / 96 h

4: DMSO; (COCl)2; Et(i-Pr)2N / CH₂Cl₂ / 1.08 h

5: NaClO₂; 2-methyl-2-butene; NaHPO₄*2H₂O / 2-methyl-propan-2-ol

6: 1.498 g / toluene; methanol; hexane

7: H₂ / Lindlar catalyst / ethyl acetate

8: 23.6 mg / pyridine

9: 95 percent / H₂NNH₂*AcOH / ethanol; toluene / 3 h

With pyridine; dmap; sodium chlorite; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; hydrazinium monoacetate; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 4: Swern oxidation;

DOI:10.1016/S0008-6215(01)00071-4

upstream raw materials:

methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate

8-bromooctanol

methyl [2-azido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate

4-methoxyphenyl O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranoside

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