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

Base Information

Chemical Name:1-p-methoxybenzyl 2,3-didehydro-4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside
CAS No.:1513847-35-2
Molecular Formula:C₃₀H₄₁ClO₁₁
Molecular Weight:613.102
Hs Code.:

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

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

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

There total 7 articles about 1-p-methoxybenzyl 2,3-didehydro-4-O-isobutyryl-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:

: C₂₆H₃₅ClO₁₀

: 79-30-1
isobutyryl chloride

: 1513847-35-2
1-p-methoxybenzyl 2,3-didehydro-4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol403369h

Reference yield:

: 1513847-28-3
C₂₀H₂₆O₈

: 1513847-35-2
1-p-methoxybenzyl 2,3-didehydro-4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 1 h / 0 °C / Inert atmosphere

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

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

4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; CeCl₃*CH₄O; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; 3.1: |Luche Cerium Reduction;
DOI:10.1021/ol403369h

Reference yield:

: 128716-41-6
4-methoxybenzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

: 1513847-35-2
1-p-methoxybenzyl 2,3-didehydro-4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 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

6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

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