O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose

Base Information

• Chemical Name: O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose
• CAS No.: 115997-40-5
• Molecular Formula: C₃₃H₃₂O₁₀
• Molecular Weight: 588.611

Synonyms:O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose

Chemical Property of O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose

There total 7 articles about O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose 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: 94.6%

O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-O-p-tolylsulfonyl-β-D-glucopyranose (104481-11-0) → O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose (115997-40-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; paraffin; for 0.0833333h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90842-5

Reference yield:

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-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose (115997-40-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) dibutyltin oxide; 2.) tetrabutylammonium iodide / 1.) toluene, 15 h, reflux; 2.) 5 h, 100 deg C

2: 98 percent / pyridine / 5 h / Ambient temperature

3: 88 percent / 1 M tetrabutylammonium fluoride / acetonitrile; H₂O; tetrahydrofuran / 10 h / Ambient temperature

4: 91.5 percent / CHCl₃; pyridine / 96 h / Ambient temperature

5: 94.6 percent / 60 percent NaH / tetrahydrofuran; dimethylformamide; paraffin / 0.08 h / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; pyridine; chloroform; water; N,N-dimethyl-formamide; acetonitrile; paraffin;

DOI:10.1016/S0008-6215(00)90842-5

Reference yield:

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-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose (115997-40-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / pyridine / 5 h / Ambient temperature

2: 88 percent / 1 M tetrabutylammonium fluoride / acetonitrile; H₂O; tetrahydrofuran / 10 h / Ambient temperature

3: 91.5 percent / CHCl₃; pyridine / 96 h / Ambient temperature

4: 94.6 percent / 60 percent NaH / tetrahydrofuran; dimethylformamide; paraffin / 0.08 h / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; pyridine; chloroform; water; N,N-dimethyl-formamide; acetonitrile; paraffin;

DOI:10.1016/S0008-6215(00)90842-5

upstream raw materials:

O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-O-p-tolylsulfonyl-β-D-glucopyranose

benzyl bromide

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

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

Downstream raw materials:

O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

O-(2-O-benzoyl-3-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

(2R,3S,4S,5R,6R)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid

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

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