methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside

Base Information

Chemical Name:methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside
CAS No.:257286-47-8
Molecular Formula:C₅₅H₆₉NO₁₅
Molecular Weight:984.151
Hs Code.:

methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside

Synonyms:methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside

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Chemical Property of methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside

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Technology Process of methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside

There total 11 articles about methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside 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: 55.0%

: 116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8
ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

: 257286-39-8
methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside

: 257286-47-8
methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo990979a

Reference yield:

: 206857-11-6
ethyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-1-thio-β-D-galactopyranoside

: 257286-47-8
methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: NaH / dimethylformamide / 4 h

2: HCl / H₂O; CH₂Cl₂

3: 91 percent / NaH / tetrahydrofuran / 3 h / 60 °C

4: 100 percent / TBAF / tetrahydrofuran / 1 h

5: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

6: 83 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 4 h / 60 °C

7: 35 percent / NaCNBH₃; molecular sieves 3 Angstroem; HCl / tetrahydrofuran; diethyl ether / 0.5 h

8: 50 percent / 2,6-di-tert-butyl-4-methylpyridine; MeOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 45 h

9: 67 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

10: 55 percent / dimethyl(methylthio)sulfonium triflate; 2,6-di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; sodium cyanoborohydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Alkylation / 2: Hydrolysis / 3: Substitution / 4: desilylation / 5: Substitution / 6: Substitution / 7: Reduction / 8: intramolecular glycosylation / 9: debenzylation / 10: glycosylation;
DOI:10.1021/jo990979a

Reference yield:

: 56245-60-4,686299-00-3
ethyl 1-thio-β-D-galactopyranoside

: 257286-47-8
methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: TsOH

2: NaH / dimethylformamide / 4 h

3: HCl / H₂O; CH₂Cl₂

4: 91 percent / NaH / tetrahydrofuran / 3 h / 60 °C

5: 100 percent / TBAF / tetrahydrofuran / 1 h

6: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

7: 83 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 4 h / 60 °C

8: 35 percent / NaCNBH₃; molecular sieves 3 Angstroem; HCl / tetrahydrofuran; diethyl ether / 0.5 h

9: 50 percent / 2,6-di-tert-butyl-4-methylpyridine; MeOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 45 h

10: 67 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

11: 55 percent / dimethyl(methylthio)sulfonium triflate; 2,6-di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Substitution / 2: Alkylation / 3: Hydrolysis / 4: Substitution / 5: desilylation / 6: Substitution / 7: Substitution / 8: Reduction / 9: intramolecular glycosylation / 10: debenzylation / 11: glycosylation;
DOI:10.1021/jo990979a