methyl O-[methyl (7,8-di-O-benzoyl-3-deoxy-α-D-manno-2-octulopyranosyl)onate]-(2->8)-(allyl 4,5-O-isopropylidene-3-deoxy-α-D-manno-2-octulopyranoside)onate

Base Information

Chemical Name:methyl O-[methyl (7,8-di-O-benzoyl-3-deoxy-α-D-manno-2-octulopyranosyl)onate]-(2->8)-(allyl 4,5-O-isopropylidene-3-deoxy-α-D-manno-2-octulopyranoside)onate
CAS No.:1327154-01-7
Molecular Formula:C₄₁H₅₀O₁₇
Molecular Weight:814.838
Hs Code.:

methyl O-[methyl (7,8-di-O-benzoyl-3-deoxy-α-D-manno-2-octulopyranosyl)onate]-(2->8)-(allyl 4,5-O-isopropylidene-3-deoxy-α-D-manno-2-octulopyranoside)onate

Synonyms:methyl O-[methyl (7,8-di-O-benzoyl-3-deoxy-α-D-manno-2-octulopyranosyl)onate]-(2->8)-(allyl 4,5-O-isopropylidene-3-deoxy-α-D-manno-2-octulopyranoside)onate

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

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

There total 5 articles about methyl O-[methyl (7,8-di-O-benzoyl-3-deoxy-α-D-manno-2-octulopyranosyl)onate]-(2->8)-(allyl 4,5-O-isopropylidene-3-deoxy-α-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: 16.0%

: 1225200-00-9
methyl (allyl 3-deoxy-4,5-O-isopropylidene-α-D-manno-oct-2-ulopyranosid)onate

: 1327153-98-9
methyl (7,8-di-O-benzoyl-4,5-O-isopropylidene-3-deoxy-D-manno-2-octulopyranosylfluoride)onate

: 1327154-01-7
methyl O-[methyl (7,8-di-O-benzoyl-3-deoxy-α-D-manno-2-octulopyranosyl)onate]-(2->8)-(allyl 4,5-O-isopropylidene-3-deoxy-α-D-manno-2-octulopyranoside)onate

Guidance literature:: With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; at -78 - -15 ℃; for 1.5h; Molecular sieve;
DOI:10.1016/j.tet.2011.06.039

Reference yield:

: C₂₆H₃₀O₁₁

: 1327154-01-7
methyl O-[methyl (7,8-di-O-benzoyl-3-deoxy-α-D-manno-2-octulopyranosyl)onate]-(2->8)-(allyl 4,5-O-isopropylidene-3-deoxy-α-D-manno-2-octulopyranoside)onate

Guidance literature:: Multi-step reaction with 4 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

3.1: sodium methylate / 18 h / 20 °C

4.1: boron trifluoride diethyl etherate; triethylamine / dichloromethane / 1.5 h / -78 - -15 °C / Molecular sieve

With thionyl chloride; boron trifluoride diethyl etherate; sodium methylate; triethylamine; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2011.06.039

Reference yield:

: C₂₆H₂₈O₉

: 1327154-01-7
methyl O-[methyl (7,8-di-O-benzoyl-3-deoxy-α-D-manno-2-octulopyranosyl)onate]-(2->8)-(allyl 4,5-O-isopropylidene-3-deoxy-α-D-manno-2-octulopyranoside)onate

Guidance literature:: Multi-step reaction with 5 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

4.1: sodium methylate / 18 h / 20 °C

5.1: boron trifluoride diethyl etherate; triethylamine / dichloromethane / 1.5 h / -78 - -15 °C / Molecular sieve

With osmium(VIII) oxide; thionyl chloride; boron trifluoride diethyl etherate; sodium methylate; 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