1-benzyl 2,3-didehydro-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside

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Chemical Name:1-benzyl 2,3-didehydro-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside
CAS No.:1513847-33-0
Molecular Formula:C₂₅H₃₃ClO₉
Molecular Weight:512.985
Hs Code.:

Synonyms:1-benzyl 2,3-didehydro-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside

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Chemical Property of 1-benzyl 2,3-didehydro-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside

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Technology Process of 1-benzyl 2,3-didehydro-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside

There total 6 articles about 1-benzyl 2,3-didehydro-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside 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: 93.0%

: 1513847-31-8
C₂₅H₃₁ClO₉

: 1513847-33-0
1-benzyl 2,3-didehydro-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside

Guidance literature:: With sodium tetrahydroborate; CeCl₃*CH₄O; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol403369h

Reference yield:

: 1513847-25-0
C₂₂H₂₈O₇

: 1513847-33-0
1-benzyl 2,3-didehydro-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: trifluoroacetic acid / water; dichloromethane / 0.17 h / 0 °C

2.1: di(n-butyl)tin oxide / toluene / 3 h / Inert atmosphere; Reflux

2.2: 1 h / 0 °C / Inert atmosphere

3.1: dmap; pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.1: CeCl₃*CH₄O; sodium tetrahydroborate / dichloromethane / 2 h / -78 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; CeCl₃*CH₄O; di(n-butyl)tin oxide; trifluoroacetic acid; In dichloromethane; water; toluene; 4.1: |Luche Cerium Reduction;
DOI:10.1021/ol403369h

Reference yield:

: 53270-14-7
benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

: 1513847-33-0
1-benzyl 2,3-didehydro-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere

2.1: trifluoroacetic acid / water; dichloromethane / 0.17 h / 0 °C

3.1: di(n-butyl)tin oxide / toluene / 3 h / Inert atmosphere; Reflux

3.2: 1 h / 0 °C / Inert atmosphere

4.1: dmap; pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

5.1: CeCl₃*CH₄O; sodium tetrahydroborate / dichloromethane / 2 h / -78 °C / Inert atmosphere

With pyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; CeCl₃*CH₄O; di(n-butyl)tin oxide; triphenylphosphine; trifluoroacetic acid; In dichloromethane; water; toluene; 5.1: |Luche Cerium Reduction;
DOI:10.1021/ol403369h