methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranoside)onate

Base Information

• Chemical Name: methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranoside)onate
• CAS No.: 1327154-04-0
• Molecular Formula: C₂₉H₃₂O₁₀
• Molecular Weight: 540.567

Synonyms:methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranoside)onate

Chemical Property of methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranoside)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranoside)onate

There total 3 articles about methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranoside)onate 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:

allyl ethyl carbonate (1469-70-1) + methyl (7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-D-manno-2-octulopyranoside)onate → methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranoside)onate (1327154-04-0) + methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-α-D-manno-2-octulopyranoside)onate (1327153-96-7)

Guidance literature:

With 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; for 23h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2011.06.039

Reference yield:

C26H30O11 → methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranoside)onate (1327154-04-0) + methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-α-D-manno-2-octulopyranoside)onate (1327153-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: thionyl chloride; triethylamine / dichloromethane / 2 h / 0 °C

1.2: 0.5 h / -78 °C

1.3: 3 h / 0 - 20 °C

2.1: 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾ / tetrahydrofuran / 23 h / Inert atmosphere; Reflux

With thionyl chloride; triethylamine; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2011.06.039

Reference yield:

C26H28O9 → methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranoside)onate (1327154-04-0) + methyl (allyl 7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-α-D-manno-2-octulopyranoside)onate (1327153-96-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 20 h / 0 °C

2.1: thionyl chloride; triethylamine / dichloromethane / 2 h / 0 °C

2.2: 0.5 h / -78 °C

2.3: 3 h / 0 - 20 °C

3.1: 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾ / tetrahydrofuran / 23 h / Inert atmosphere; Reflux

With osmium(VIII) oxide; thionyl chloride; 4-methylmorpholine N-oxide; triethylamine; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1016/j.tet.2011.06.039

upstream raw materials:

allyl ethyl carbonate

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