(2S,3R,4R,E)-1,3-bis(benzyloxy)-5-(but-3-enylamino)-7-phenylhept-6-ene-2,4-diol

Base Information

Chemical Name:(2S,3R,4R,E)-1,3-bis(benzyloxy)-5-(but-3-enylamino)-7-phenylhept-6-ene-2,4-diol
CAS No.:1439372-89-0
Molecular Formula:C₃₁H₃₇NO₄
Molecular Weight:487.639
Hs Code.:

Synonyms:(2S,3R,4R,E)-1,3-bis(benzyloxy)-5-(but-3-enylamino)-7-phenylhept-6-ene-2,4-diol

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Chemical Property of (2S,3R,4R,E)-1,3-bis(benzyloxy)-5-(but-3-enylamino)-7-phenylhept-6-ene-2,4-diol

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Technology Process of (2S,3R,4R,E)-1,3-bis(benzyloxy)-5-(but-3-enylamino)-7-phenylhept-6-ene-2,4-diol

There total 5 articles about (2S,3R,4R,E)-1,3-bis(benzyloxy)-5-(but-3-enylamino)-7-phenylhept-6-ene-2,4-diol 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: 59.0%

: 6783-05-7
trans-2-phenylvinylboronic acid

: (3S,4R,5S)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol

: 17875-18-2
but-3-en-1-amine hydrochloride

: 1439372-89-0
(2S,3R,4R,E)-1,3-bis(benzyloxy)-5-(but-3-enylamino)-7-phenylhept-6-ene-2,4-diol

Guidance literature:: With triethylamine; In ethanol; at 25 ℃; for 96h;
DOI:10.1039/c3ob40374b

Reference yield:

: 144490-03-9
1,2,3,5-tetra-O-acetyl-β-L-ribofuranose

: 1439372-89-0
(2S,3R,4R,E)-1,3-bis(benzyloxy)-5-(but-3-enylamino)-7-phenylhept-6-ene-2,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: dichloromethane; hexane / 15 h / 0 - 25 °C / Inert atmosphere

2.1: potassium carbonate; methanol / 2 h / 25 °C

3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere; Reflux

3.2: 0.5 h / 25 °C / Reflux

4.1: acetic acid / water / 2 h / 112 °C

5.1: triethylamine / ethanol / 96 h / 25 °C

With methanol; sodium hydride; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; mineral oil;
DOI:10.1039/c3ob40374b

Reference yield:

: 1439372-63-0
((3aS,5S,6S,6aS)-6-acetoxy-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methyl acetate

: 1439372-89-0
(2S,3R,4R,E)-1,3-bis(benzyloxy)-5-(but-3-enylamino)-7-phenylhept-6-ene-2,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium carbonate; methanol / 2 h / 25 °C

2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere; Reflux

2.2: 0.5 h / 25 °C / Reflux

3.1: acetic acid / water / 2 h / 112 °C

4.1: triethylamine / ethanol / 96 h / 25 °C

With methanol; sodium hydride; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; ethanol; water; mineral oil;
DOI:10.1039/c3ob40374b