2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose
• CAS No.: 444709-80-2
• Molecular Formula: C₄₉H₄₄O₁₅
• Molecular Weight: 872.879

Synonyms:2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose

Chemical Property of 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose

Chemical Property:

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Technology Process of 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose

There total 3 articles about 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-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: 83.0%

2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (183901-63-5) + 4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose (444709-74-4) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose (444709-80-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0957-4166(02)00107-6

Reference yield:

benzaldehyde (100-52-7) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose (444709-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid monohydrate; triethyl orthoformate / dimethylformamide / 12 h / 20 °C

2: 83 percent / TMSOTf / CH₂Cl₂ / 2 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; orthoformic acid triethyl ester; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(02)00107-6

Reference yield:

1,2-O-ethylidene-(R,S)-β-D-mannopyranose (230953-16-9) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose (444709-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid monohydrate; triethyl orthoformate / dimethylformamide / 12 h / 20 °C

2: 83 percent / TMSOTf / CH₂Cl₂ / 2 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; orthoformic acid triethyl ester; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(02)00107-6

upstream raw materials:

2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate

4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose

benzaldehyde

1,2-O-ethylidene-(R,S)-β-D-mannopyranose

Downstream raw materials:

2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-1,2-O-ethylidene-β-D-mannopyranose

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