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)

Base Information

Chemical Name: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)
CAS No.:273749-63-6
Molecular Formula:C₄₂H₄₅N₃O₁₁
Molecular Weight:767.833
Hs Code.:

Synonyms: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)

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Chemical Property of 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)

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Technology Process of 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)

There total 12 articles about 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) 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: 82.0%

: 100-39-0
benzyl bromide

: 273749-73-8
(2R,4aR,6R,7R,8R,8aS)-6-((2R,4aR,6R,7R,8R,8aS)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 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)

Guidance literature:: (2R,4aR,6R,7R,8R,8aS)-6-((2R,4aR,6R,7R,8R,8aS)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol; With sodium hydride; In N,N-dimethyl-formamide;

benzyl bromide; In N,N-dimethyl-formamide; at 0 ℃; for 6h; Further stages.;
DOI:10.1021/ol0057075

Reference yield:

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

: 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)

Guidance literature:: Multi-step reaction with 4 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

With lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; sodium hydride; toluene-4-sulfonic 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;
DOI:10.1021/ol0057075

Reference yield:

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

: 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)

Guidance literature:: Multi-step reaction with 3 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

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