4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranose

Base Information

Chemical Name:4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranose
CAS No.:1312108-33-0
Molecular Formula:C₃₁H₃₉NO₁₇
Molecular Weight:697.647
Hs Code.:

Synonyms:4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranose

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranose

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranose

There total 9 articles about 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranose 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: 64.0%

: 1312108-29-4
allyl 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

: 1312108-33-0
4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranose

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; at 80 ℃;
DOI:10.1002/anie.201811403

Reference yield:

: 64650-81-3
allyl α-L-rhamnopyranoside

: 1312108-33-0
4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranose

Guidance literature:: Multi-step reaction with 7 steps

1.1: camphor-10-sulfonic acid / dichloromethane / 0.5 h / 21 °C

2.1: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 21 °C / Inert atmosphere

2.2: 3 h / 0 - 21 °C / Inert atmosphere

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

4.1: toluene / Distillation

4.2: 0.83 h / -78 - 21 °C / Inert atmosphere

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

6.1: pyridine / 16 h / 21 °C

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

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; camphor-10-sulfonic acid; water; acetic acid; ethylenediamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene; butan-1-ol;
DOI:10.1021/ol2013704

Reference yield:

: 87190-67-8
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate

: 1312108-33-0
4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: toluene / Distillation

1.2: 0.83 h / -78 - 21 °C / Inert atmosphere

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

3.1: pyridine / 16 h / 21 °C

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

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; ethylenediamine; In toluene; butan-1-ol;
DOI:10.1021/ol2013704