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

Base Information

Chemical Name:methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate
CAS No.:351530-33-1
Molecular Formula:C₅₃H₆₃Cl₃N₂O₁₇
Molecular Weight:1106.45
Hs Code.:

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

Synonyms:methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate

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Chemical Property of methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate

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Technology Process of methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate

There total 12 articles about methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]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: 88.0%

: 545-06-2
trichloroacetonitrile

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

: 351530-33-1
methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0008-6215(01)00071-4

Reference yield:

: 50816-19-8
8-bromooctanol

: 351530-33-1
methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate

Guidance literature:: Multi-step reaction with 10 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: 77 percent / cerium(IV) ammonium nitrate / acetonitrile / 1.5 h / 0 °C

10: 88 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

With pyridine; dmap; sodium chlorite; 2-methyl-but-2-ene; oxalyl dichloride; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 4: Swern oxidation;
DOI:10.1016/S0008-6215(01)00071-4

Reference yield:

: 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

: 351530-33-1
methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / Lindlar catalyst / ethyl acetate

2: 23.6 mg / pyridine

3: 77 percent / cerium(IV) ammonium nitrate / acetonitrile / 1.5 h / 0 °C

4: 88 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

With pyridine; ammonium cerium(IV) nitrate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; Lindlar's catalyst; In dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1016/S0008-6215(01)00071-4