(-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide

Base Information

Chemical Name:(-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide
CAS No.:1410798-42-3
Molecular Formula:C₄₁H₆₉NO₁₂Si₂
Molecular Weight:824.169
Hs Code.:

(-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide

Synonyms:(-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide

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Chemical Property of (-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide

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Technology Process of (-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide

There total 13 articles about (-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide 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: 70.0%

: 60505-07-9,150131-68-3,122872-31-5
2,2,8-trimethyl-3a,3b,6a,6b,9a,9b-hexahydro-1,3,4,6,7-pentaoxa-9-aza-trindene

: 1410798-41-2
(-)-(2E)-3-[4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxy-phenyl]-2-methylacrylic acid

: 1410798-42-3
(-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1002/anie.200902840

Reference yield:

: 1190266-98-8
(E)-methyl 3-(3-(allyloxy)-4-hydroxyphenyl)-2-methylacrylate

: 1410798-42-3
(-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide

Guidance literature:: Multi-step reaction with 3 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 3 h / 60 °C / Inert atmosphere

2: dimethylsulfide; aluminum tri-bromide / dichloromethane / 5.5 h / 5 - 10 °C / Inert atmosphere

3: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

With aluminum tri-bromide; dimethylsulfide; di-isopropyl azodicarboxylate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: |Mitsunobu Displacement;
DOI:10.1021/ol3028237

Reference yield:

: 1410798-30-9
2,2,7-trimethyl-3a,4,5,5a,8a,8b-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[2,1-d]oxazole-4,5-diol

: 1410798-42-3
(-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetra-(n-butyl)ammonium iodide / dichloromethane / 20 °C

1.2: 4.5 h / 35 - 40 °C

2.1: acetic acid / water / 12 h / 50 °C

2.2: 4 h / 20 - 80 °C

3.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

With tetra-(n-butyl)ammonium iodide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol3028237