dibenzyl (3S,4R,5E)-(3-azido-4-O-benzyloxymethyl-4-hydroxynonadec-5-en-1-yl)phosphonate

Base Information

Chemical Name:dibenzyl (3S,4R,5E)-(3-azido-4-O-benzyloxymethyl-4-hydroxynonadec-5-en-1-yl)phosphonate
CAS No.:851915-74-7
Molecular Formula:C₄₁H₅₈N₃O₅P
Molecular Weight:703.902
Hs Code.:

Synonyms:dibenzyl (3S,4R,5E)-(3-azido-4-O-benzyloxymethyl-4-hydroxynonadec-5-en-1-yl)phosphonate

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Chemical Property of dibenzyl (3S,4R,5E)-(3-azido-4-O-benzyloxymethyl-4-hydroxynonadec-5-en-1-yl)phosphonate

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Technology Process of dibenzyl (3S,4R,5E)-(3-azido-4-O-benzyloxymethyl-4-hydroxynonadec-5-en-1-yl)phosphonate

There total 6 articles about dibenzyl (3S,4R,5E)-(3-azido-4-O-benzyloxymethyl-4-hydroxynonadec-5-en-1-yl)phosphonate 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: 83.0%

: 851915-73-6
dibenzyl (3R,4R,5E)-(4-O-benzyloxymethyl-3,4-dihydroxynonadec-5-en-1-yl)phosphonate

: 851915-74-7
dibenzyl (3S,4R,5E)-(3-azido-4-O-benzyloxymethyl-4-hydroxynonadec-5-en-1-yl)phosphonate

Guidance literature:: With Zn(N₃)2/bis-pyridine complex; di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 50 ℃; for 5h;
DOI:10.1002/ejoc.200400671

Reference yield:

: 851915-71-4
(2R,3R,4E)-1,2-anhydrooctadec-4-ene-1,2,3-triol

: 851915-74-7
dibenzyl (3S,4R,5E)-(3-azido-4-O-benzyloxymethyl-4-hydroxynonadec-5-en-1-yl)phosphonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 48 h / 20 °C

2.1: butyllithium; BF₃*OEt₂ / tetrahydrofuran; hexane / 2.5 h / -80 °C

2.2: 90 percent / tetrahydrofuran; hexane / 2 h

3.1: 83 percent / Zn(N₃)2*Pyr₂; PPh₃; DIAD / toluene / 5 h / 50 °C

With n-butyllithium; Zn(N₃)2/bis-pyridine complex; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; toluene; 3.1: Mitsunobu reaction;
DOI:10.1002/ejoc.200400671

Reference yield:

: 851915-72-5
(2R,3R,4E)-1,2-anhydro-3-O-(benzyloxymethyl)octadec-4-ene-1,2,3-triol

: 851915-74-7
dibenzyl (3S,4R,5E)-(3-azido-4-O-benzyloxymethyl-4-hydroxynonadec-5-en-1-yl)phosphonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: butyllithium; BF₃*OEt₂ / tetrahydrofuran; hexane / 2.5 h / -80 °C

1.2: 90 percent / tetrahydrofuran; hexane / 2 h

2.1: 83 percent / Zn(N₃)2*Pyr₂; PPh₃; DIAD / toluene / 5 h / 50 °C

With n-butyllithium; Zn(N₃)2/bis-pyridine complex; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; triphenylphosphine; In tetrahydrofuran; hexane; toluene; 2.1: Mitsunobu reaction;
DOI:10.1002/ejoc.200400671