(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(2-acetoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol

Base Information

Chemical Name:(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(2-acetoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol
CAS No.:1443119-75-2
Molecular Formula:C₃₅H₃₆O₁₃
Molecular Weight:664.663
Hs Code.:

Synonyms:(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(2-acetoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol

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Chemical Property of (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(2-acetoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol

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Technology Process of (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(2-acetoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol

There total 7 articles about (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(2-acetoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol 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: 47.0%

: (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-[2-acetyloxy-5-(bromomethyl)phenyl]-D-glucitol

: 54798-16-2
methyl 2-chloroazulene-1-carboxylate

: 1443119-75-2
(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(2-acetoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol

Guidance literature:: (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-[2-acetyloxy-5-(bromomethyl)phenyl]-D-glucitol; With chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; at 80 ℃; for 0.5h;

methyl 2-chloroazulene-1-carboxylate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 2h; Reflux;
DOI:10.1016/j.bmc.2013.03.067

Reference yield:

: C₁₃H₁₈O₆

: 1443119-75-2
(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(2-acetoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / 20 °C

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / ethyl acetate / 1 h / Reflux

3.1: zinc; ethylene dibromide; chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 80 °C

3.2: 2 h / Reflux

With N-Bromosuccinimide; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); ethylene dibromide; zinc; In tetrahydrofuran; pyridine; ethyl acetate; 3.2: |Negishi Coupling;
DOI:10.1016/j.bmc.2013.03.067

Reference yield:

: (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-[2-(acetyloxy)-5-methylphenyl]-D-glucitol

: 1443119-75-2
(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(2-acetoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / ethyl acetate / 1 h / Reflux

2.1: zinc; ethylene dibromide; chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 80 °C

2.2: 2 h / Reflux

With N-Bromosuccinimide; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); ethylene dibromide; zinc; In tetrahydrofuran; ethyl acetate; 2.2: |Negishi Coupling;
DOI:10.1016/j.bmc.2013.03.067