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

Base Information

• Chemical Name: 1-benzyl 4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside
• CAS No.: 1513847-38-5
• Molecular Formula: C₂₉H₄₁ClO₁₂
• Molecular Weight: 617.09

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

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

Chemical Property:

Purity/Quality:

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

There total 8 articles about 1-benzyl 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: 84.0%

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) → 1-benzyl 4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside (1513847-38-5)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 0 - 20 ℃;

DOI:10.1021/ol403369h

Reference yield:

C22H28O7 (1513847-25-0) → 1-benzyl 4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside (1513847-38-5)

Guidance literature:

Multi-step reaction with 6 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

6.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tert-butyl alcohol; acetone / 0 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; CeCl₃*CH₄O; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; trifluoroacetic acid; In dichloromethane; water; acetone; toluene; tert-butyl alcohol; 4.1: |Luche Cerium Reduction / 6.1: |Upjohn Dihydroxylation;

DOI:10.1021/ol403369h

Reference yield:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (53270-14-7) → 1-benzyl 4-O-isobutyryl-α-L-rhamnopyranosyl-(1→4)-2-O-chloroacetyl-3-O-isobutyryl-α-L-rhamnopyranoside (1513847-38-5)

Guidance literature:

Multi-step reaction with 7 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

7.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tert-butyl alcohol; acetone / 0 - 20 °C

With pyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; osmium(VIII) oxide; CeCl₃*CH₄O; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; triphenylphosphine; trifluoroacetic acid; In dichloromethane; water; acetone; toluene; tert-butyl alcohol; 5.1: |Luche Cerium Reduction / 7.1: |Upjohn Dihydroxylation;

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

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