methyl O-(2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:methyl O-(2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
CAS No.:273749-62-5
Molecular Formula:C₃₈H₄₉N₃O₁₃
Molecular Weight:755.819
Hs Code.:

Synonyms:methyl O-(2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

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Chemical Property of methyl O-(2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

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Technology Process of methyl O-(2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

There total 9 articles about methyl O-(2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-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: 83.0%

: phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranosyl sulfoxide

: 274260-02-5
methyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 273749-62-5
methyl O-(2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; In dichloromethane; at -60 - -30 ℃; for 1h;
DOI:10.1021/ol0057075

Reference yield:

: (2R,3S,4R)-5-Azido-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol

: 273749-62-5
methyl O-(2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 424 mg / p-TsOH*H₂O / acetonitrile / 6 h / 20 °C

2: 83 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -60 - -30 °C

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; toluene-4-sulfonic acid; In dichloromethane; acetonitrile; 1: Deacetylation / 2: Condensation;
DOI:10.1021/ol0057075

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 273749-62-5
methyl O-(2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

2: 92 percent / DMAP / pyridine / 12 h / Heating

3: 69 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.33 h / -78 °C

4: 83 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -60 - -30 °C

With dmap; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Acylation / 3: Oxidation / 4: Condensation;
DOI:10.1021/ol0057075