4-pentenyl O-(3-O-benzyl-4,6-O-benzylidene-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:4-pentenyl O-(3-O-benzyl-4,6-O-benzylidene-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:199115-82-7
Molecular Formula:C₆₁H₅₈N₂O₁₃
Molecular Weight:1027.14
Hs Code.:

4-pentenyl O-(3-O-benzyl-4,6-O-benzylidene-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Synonyms:4-pentenyl O-(3-O-benzyl-4,6-O-benzylidene-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of 4-pentenyl O-(3-O-benzyl-4,6-O-benzylidene-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of 4-pentenyl O-(3-O-benzyl-4,6-O-benzylidene-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 6 articles about 4-pentenyl O-(3-O-benzyl-4,6-O-benzylidene-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-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: 72.1%

: 100-39-0
benzyl bromide

: 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

: 199115-82-7
4-pentenyl O-(3-O-benzyl-4,6-O-benzylidene-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 5.5h;
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

: 199115-82-7
4-pentenyl O-(3-O-benzyl-4,6-O-benzylidene-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 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

4: 72.1 percent / n-Bu₄NI; sodium hydride / dimethylformamide / 5.5 h / 20 °C

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; (+)-10-camphorsulfonic acid; triethylamine; In methanol; ethanol; N,N-dimethyl-formamide; 1: acetalization / 2: Deacetylation / 3: Acylation / 4: Alkylation;
DOI:10.1246/bcsj.73.163

Reference yield:

: (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

: 199115-82-7
4-pentenyl O-(3-O-benzyl-4,6-O-benzylidene-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 3.55 g / triethylamine / methanol; dimethylformamide / 39.5 h / 20 - 120 °C

2: 72.1 percent / n-Bu₄NI; sodium hydride / dimethylformamide / 5.5 h / 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In methanol; N,N-dimethyl-formamide; 1: Acylation / 2: Alkylation;
DOI:10.1246/bcsj.73.163