cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

Base Information

Chemical Name:cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside
CAS No.:1312108-50-1
Molecular Formula:C₄₈H₇₃NO₁₂
Molecular Weight:856.107
Hs Code.:

Synonyms:cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

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Chemical Property of cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

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Technology Process of cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

There total 16 articles about cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-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: 65.0%

: 1312108-44-3
cholesteryl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

: 1312108-50-1
cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

Guidance literature:: With methanol; acetyl chloride; In dichloromethane; at 21 ℃; for 36h; Inert atmosphere;
DOI:10.1021/ol2013704

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 1312108-50-1
cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1.1: acetic acid; ethylenediamine / tetrahydrofuran / 16 h / 21 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

3.1: toluene / Distillation

3.2: 0.83 h / -78 - 21 °C / Inert atmosphere

4.1: ethylenediamine / butan-1-ol / 2 h / 85 °C

5.1: pyridine / 16 h / 21 °C

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid / 0.5 h / 80 °C / Inert atmosphere

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.1: toluene / Distillation

8.2: 1 h / 0 - 21 °C / Inert atmosphere; Molecular sieve

9.1: methanol; acetyl chloride / dichloromethane / 36 h / 21 °C / Inert atmosphere

With pyridine; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; acetyl chloride; In tetrahydrofuran; dichloromethane; toluene; butan-1-ol;
DOI:10.1021/ol2013704

Reference yield:

: 1312108-09-0
allyl 4-O-(3-acetoxybenzoyl)-2,3-O-methylorthoacetyl-α-L-rhamnopyranoside

: 1312108-50-1
cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: water / tetrahydrofuran / 0.5 h / 21 °C

2.1: toluene / Distillation

2.2: 0.83 h / -78 - 21 °C / Inert atmosphere

3.1: ethylenediamine / butan-1-ol / 2 h / 85 °C

4.1: pyridine / 16 h / 21 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid / 0.5 h / 80 °C / Inert atmosphere

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

7.1: toluene / Distillation

7.2: 1 h / 0 - 21 °C / Inert atmosphere; Molecular sieve

8.1: methanol; acetyl chloride / dichloromethane / 36 h / 21 °C / Inert atmosphere

With pyridine; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; acetyl chloride; In tetrahydrofuran; dichloromethane; toluene; butan-1-ol;
DOI:10.1021/ol2013704