O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

Base Information

• Chemical Name: O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose
• CAS No.: 97390-32-4
• Molecular Formula: C₃₈H₅₆O₁₁Si₂
• Molecular Weight: 745.027

Synonyms:O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

Chemical Property of O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

Chemical Property:

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Technology Process of O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

There total 9 articles about O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose 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: 26.0%

benzyl bromide (100-39-0) + 1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-18-6) → O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-32-4) + O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-26-6,99571-45-6) + (2R,4aR,6S,7R,8S,8aS)-7-Benzyloxy-2-phenyl-6-((1R,2R,8S,9R,10R)-4,4,6,6-tetraisopropyl-3,5,7,12,13-pentaoxa-4,6-disila-tricyclo[8.2.1.02,8]tridec-9-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (97390-31-3)

Guidance literature:

With silver(l) oxide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/0008-6215(85)85222-8

Reference yield: 6.0%

benzyl trifluoromethyl sulfone (4855-02-1) + 1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-18-6) → O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-32-4) + O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-26-6,99571-45-6) + (2R,4aR,6S,7R,8S,8aS)-7-Benzyloxy-2-phenyl-6-((1R,2R,8S,9R,10R)-4,4,6,6-tetraisopropyl-3,5,7,12,13-pentaoxa-4,6-disila-tricyclo[8.2.1.02,8]tridec-9-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (97390-31-3)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In dichloromethane; at -60 ℃;

DOI:10.1016/0008-6215(85)85222-8

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-32-4)

Guidance literature:

Multi-step reaction with 4 steps

1: p-toluenesulfonic acid monohydrate / dimethylformamide / 1.5 h / 75 - 80 °C

2: 1.) pyridine; 2.) pyridine / 1.) r.t., 10 h; 2.) r.t., 6 h

3: 94 percent / hydrazine monohydrate / methanol; various solvent(s) / 10 h / Ambient temperature

4: 10 percent / 2,4,6-collidine / CH₂Cl₂ / -60 °C

With pyridine; 2,4,6-trimethyl-pyridine; toluene-4-sulfonic acid; hydrazine hydrate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(85)85222-8

upstream raw materials:

benzyl trifluoromethyl sulfone

1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

benzyl bromide

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

Downstream raw materials:

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R)-2-Acetoxymethyl-5-azido-4-benzyloxy-6-bromo-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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