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

Base Information

Chemical Name: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
CAS No.:1312108-29-4
Molecular Formula:C₃₄H₄₃NO₁₇
Molecular Weight:737.712
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 10 articles about 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 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%

: 1312108-20-5
allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

: 108-24-7
acetic anhydride

: 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

Guidance literature:: allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-L-rhamnopyranoside; With ethylenediamine; In butan-1-ol; at 85 ℃;

acetic anhydride; With pyridine; at 20 ℃;
DOI:10.1002/anie.201811403

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; camphor-10-sulfonic acid; water; 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

: 1312108-29-4
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

Guidance literature:: Multi-step reaction with 3 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

With pyridine; ethylenediamine; In toluene; butan-1-ol;
DOI:10.1021/ol2013704