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

Base Information

Chemical Name: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
CAS No.:351530-30-8
Molecular Formula:C₅₆H₆₅N₃O₁₇
Molecular Weight:1052.14
Hs Code.:

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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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:

: 50816-19-8
8-bromooctanol

: 351530-30-8
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

Guidance literature:: Multi-step reaction with 6 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

With dmap; sodium chlorite; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; 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

: 351530-30-8
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

Guidance literature:: Multi-step reaction with 6 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

With dmap; sodium chlorite; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; 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-3-O-levulinoyl-β-D-galactopyranosyl)-(1->4)-6-O-tert-butyldiphenylsilyl-2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranoside

: 351530-30-8
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

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / H₂NNH₂*AcOH / ethanol; toluene / 1.17 h

2: 53 percent / NaH / dimethylformamide / 5 h / -50 - 0 °C

3: 96 percent / DMAP / 1,2-dichloro-ethane; pyridine / 4 h

4: 80 percent / TBAF / tetrahydrofuran / 96 h

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

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

7: 1.498 g / toluene; methanol; hexane

With dmap; sodium chlorite; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrazinium monoacetate; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 5: Swern oxidation;
DOI:10.1016/S0008-6215(01)00071-4