(2R,3R,4R)-1,3-O-[(S)-benzylidene]-2-(4-methoxybenzyloxy)-11-octadecyn-4-ol

Base Information

Chemical Name:(2R,3R,4R)-1,3-O-[(S)-benzylidene]-2-(4-methoxybenzyloxy)-11-octadecyn-4-ol
CAS No.:1215176-43-4
Molecular Formula:C₃₃H₄₆O₅
Molecular Weight:522.725
Hs Code.:

Synonyms:(2R,3R,4R)-1,3-O-[(S)-benzylidene]-2-(4-methoxybenzyloxy)-11-octadecyn-4-ol

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Chemical Property of (2R,3R,4R)-1,3-O-[(S)-benzylidene]-2-(4-methoxybenzyloxy)-11-octadecyn-4-ol

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Technology Process of (2R,3R,4R)-1,3-O-[(S)-benzylidene]-2-(4-methoxybenzyloxy)-11-octadecyn-4-ol

There total 7 articles about (2R,3R,4R)-1,3-O-[(S)-benzylidene]-2-(4-methoxybenzyloxy)-11-octadecyn-4-ol 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: 94.0%

: 1215176-38-7
1-iodo-6-tridecyne

: 1215176-21-8
4,5-anhydro-1,3-O-benzylidene-2-O-(4-methoxybenzyl)-D-arabinitol

: 1215176-43-4
(2R,3R,4R)-1,3-O-[(S)-benzylidene]-2-(4-methoxybenzyloxy)-11-octadecyn-4-ol

Guidance literature:: 1-iodo-6-tridecyne; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - 20 ℃; for 1.08333h; Inert atmosphere;

With copper(l) iodide; In tetrahydrofuran; diethyl ether; pentane; at -40 - -30 ℃; for 0.5h; Inert atmosphere;

4,5-anhydro-1,3-O-benzylidene-2-O-(4-methoxybenzyl)-D-arabinitol; In tetrahydrofuran; diethyl ether; pentane; at -20 - 30 ℃; for 16h;

Reference yield: 94.0%

: 7681-65-4
copper(l) iodide

: 1215176-38-7
1-iodo-6-tridecyne

: 1215176-21-8
4,5-anhydro-1,3-O-benzylidene-2-O-(4-methoxybenzyl)-D-arabinitol

: 1215176-43-4
(2R,3R,4R)-1,3-O-[(S)-benzylidene]-2-(4-methoxybenzyloxy)-11-octadecyn-4-ol

Guidance literature:: 1-iodo-6-tridecyne; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - 20 ℃; Inert atmosphere;

copper(l) iodide; In tetrahydrofuran; diethyl ether; pentane; at -40 - -30 ℃; Inert atmosphere;

4,5-anhydro-1,3-O-benzylidene-2-O-(4-methoxybenzyl)-D-arabinitol; In tetrahydrofuran; diethyl ether; pentane; at -30 - 20 ℃;
DOI:10.1016/j.carres.2010.05.003

Reference yield:

: 37011-87-3
2-tridec-6-ynyloxy-tetrahydro-pyran

: 1215176-43-4
(2R,3R,4R)-1,3-O-[(S)-benzylidene]-2-(4-methoxybenzyloxy)-11-octadecyn-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid; methanol / 6 h / 20 - 30 °C

2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.5 h / 0 °C

2.2: 16 h / Reflux

3.1: tert.-butyl lithium / diethyl ether; pentane / 1.08 h / -78 - 20 °C / Inert atmosphere

3.2: 0.5 h / -40 - -30 °C / Inert atmosphere

3.3: 16 h / -20 - 30 °C

With methanol; tert.-butyl lithium; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; In diethyl ether; dichloromethane; pentane;