1-benzyl 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-benzyl 2,3-didehydro-4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside
• CAS No.: 1513847-34-1
• Molecular Formula: C₂₉H₃₉ClO₁₀
• Molecular Weight: 583.076

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

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

Chemical Property:

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Technology Process of 1-benzyl 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-benzyl 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: 93.0%

1-benzyl 2,3-didehydro-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside (1513847-33-0) + isobutyryl chloride (79-30-1) → 1-benzyl 2,3-didehydro-4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside (1513847-34-1)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol403369h

Reference yield:

C22H28O7 (1513847-25-0) → 1-benzyl 2,3-didehydro-4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside (1513847-34-1)

Guidance literature:

Multi-step reaction with 5 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

5.1: dmap; pyridine / dichloromethane / 2 h / 0 - 20 °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:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (53270-14-7) → 1-benzyl 2,3-didehydro-4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside (1513847-34-1)

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; pyridine / 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; triphenylphosphine; trifluoroacetic acid; In dichloromethane; water; toluene; 5.1: |Luche Cerium Reduction;

DOI:10.1021/ol403369h

upstream raw materials:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

C₂₂H₂₈O₇

C₁₉H₂₄O₇

C₂₃H₃₀O₈

Downstream raw materials:

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

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

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