methyl O-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-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-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
CAS No.:273749-64-7
Molecular Formula:C₄₂H₄₇N₃O₁₁
Molecular Weight:769.849
Hs Code.:

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

There total 13 articles about methyl O-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-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: 91.0%

: 273749-63-6
methyl O-(2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-(2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside)

: 273749-64-7
methyl O-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Guidance literature:: With 3 A molecular sieve; sodium cyanoborohydride; trifluoroacetic acid; In N,N-dimethyl-formamide; at 0 ℃; for 8h;
DOI:10.1021/ol0057075

Reference yield:

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

: 273749-64-7
methyl O-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 424 mg / p-TsOH*H₂O / acetonitrile / 6 h / 20 °C

2.1: 83 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -60 - -30 °C

3.1: 442 mg / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 24 h / 60 °C

4.1: NaH / dimethylformamide; various solvent(s)

4.2: 82 percent / dimethylformamide; various solvent(s) / 6 h / 0 °C

5.1: 91 percent / NaBH₃CN; TFA; 3 Angstroem molecular sieves / dimethylformamide / 8 h / 0 °C

With lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 3 A molecular sieve; 4 A molecular sieve; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Deacetylation / 2.1: Condensation / 3.1: Hydrolysis / 4.1: Metallation / 4.2: Benzylation / 5.1: Reduction;
DOI:10.1021/ol0057075

Reference yield:

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

: 273749-64-7
methyl O-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 83 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -60 - -30 °C

2.1: 442 mg / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 24 h / 60 °C

3.1: NaH / dimethylformamide; various solvent(s)

3.2: 82 percent / dimethylformamide; various solvent(s) / 6 h / 0 °C

4.1: 91 percent / NaBH₃CN; TFA; 3 Angstroem molecular sieves / dimethylformamide / 8 h / 0 °C

With lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 3 A molecular sieve; 4 A molecular sieve; sodium hydride; sodium cyanoborohydride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Condensation / 2.1: Hydrolysis / 3.1: Metallation / 3.2: Benzylation / 4.1: Reduction;
DOI:10.1021/ol0057075