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

Base Information

Chemical Name: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
CAS No.:1312108-20-5
Molecular Formula:C₄₀H₄₃NO₁₈
Molecular Weight:825.777
Hs Code.:

Synonyms: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

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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-phthalimido-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-phthalimido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

There total 7 articles about 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 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: 94.0%

: 1312108-00-1
allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-α-L-rhamnopyranoside

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

: 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

Guidance literature:: allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-α-L-rhamnopyranoside; 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate; In toluene; Distillation;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 21 ℃; for 0.833333h; Inert atmosphere;
DOI:10.1021/ol2013704

Reference yield:

: 85-44-9
phthalic anhydride

: 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

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydrogencarbonate; sodium hydroxide / methanol; water; acetone / 0 - 21 °C

2.1: pyridine / 16 h / 21 °C

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

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

5.1: toluene / Distillation

5.2: 0.83 h / -78 - 21 °C / Inert atmosphere

With pyridine; sodium hydrogencarbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene;
DOI:10.1021/ol2013704

Reference yield:

: allyl 2,3-O-methylorthoacetyl-α-L-rhamnopyranoside

: 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

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 3 h / 0 - 21 °C / Inert atmosphere

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

3.1: toluene / Distillation

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

With water; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ol2013704