4-pentenyl O-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:4-pentenyl O-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:199115-81-6
Molecular Formula:C₄₀H₄₀N₂O₁₃
Molecular Weight:756.763
Hs Code.:

Synonyms:4-pentenyl O-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of 4-pentenyl O-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of 4-pentenyl O-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 5 articles about 4-pentenyl O-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-deoxy-2-phthalimido-β-D-glucopyranoside 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:

: 85-44-9
phthalic anhydride

: (2R,4aR,6S,7R,8R,8aS)-7-Amino-6-((2R,3S,4R,5R,6R)-5-amino-4-hydroxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: 199115-81-6
4-pentenyl O-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With triethylamine; In methanol; N,N-dimethyl-formamide; at 20 - 120 ℃; for 39.5h;
DOI:10.1246/bcsj.73.163

Reference yield:

: 199115-80-5
N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-5-Acetylamino-4-hydroxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

: 199115-81-6
4-pentenyl O-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: aq. NaOH / ethanol / 48 h / 100 °C

2: 3.55 g / triethylamine / methanol; dimethylformamide / 39.5 h / 20 - 120 °C

With sodium hydroxide; triethylamine; In methanol; ethanol; N,N-dimethyl-formamide; 1: Deacetylation / 2: Acylation;
DOI:10.1246/bcsj.73.163

Reference yield:

: N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-hydroxy-6-hydroxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yl]-acetamide

: 199115-81-6
4-pentenyl O-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: (+)-10-camphorsulfonic acid / dimethylformamide / 28 h / 20 °C / 18.75 Torr

2: aq. NaOH / ethanol / 48 h / 100 °C

3: 3.55 g / triethylamine / methanol; dimethylformamide / 39.5 h / 20 - 120 °C

With sodium hydroxide; (+)-10-camphorsulfonic acid; triethylamine; In methanol; ethanol; N,N-dimethyl-formamide; 1: acetalization / 2: Deacetylation / 3: Acylation;
DOI:10.1246/bcsj.73.163