(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-methoxy-2-oxoethyl)-2-((4-methoxybenzyloxy)methyl)tetrahydrofuran-3-yl hexanoate

Base Information

Chemical Name:(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-methoxy-2-oxoethyl)-2-((4-methoxybenzyloxy)methyl)tetrahydrofuran-3-yl hexanoate
CAS No.:1426310-22-6
Molecular Formula:C₂₈H₄₆O₈Si
Molecular Weight:538.754
Hs Code.:

Synonyms:(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-methoxy-2-oxoethyl)-2-((4-methoxybenzyloxy)methyl)tetrahydrofuran-3-yl hexanoate

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Chemical Property of (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-methoxy-2-oxoethyl)-2-((4-methoxybenzyloxy)methyl)tetrahydrofuran-3-yl hexanoate

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Technology Process of (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-methoxy-2-oxoethyl)-2-((4-methoxybenzyloxy)methyl)tetrahydrofuran-3-yl hexanoate

There total 9 articles about (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-methoxy-2-oxoethyl)-2-((4-methoxybenzyloxy)methyl)tetrahydrofuran-3-yl hexanoate 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: 71.0%

: 1426310-18-0
methyl 2-((2R,3R,4R)-4-(tertbutyldimethylsilyloxy)-3-hydroxy-2-((4-methoxybenzyloxy)methyl)-tetrahydrofuran-2-yl)acetate

: 142-61-0
Hexanoyl chloride

: 1426310-22-6
(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-methoxy-2-oxoethyl)-2-((4-methoxybenzyloxy)methyl)tetrahydrofuran-3-yl hexanoate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 5.5h;
DOI:10.1021/ol4001894

Reference yield:

: 1426310-12-4
(S,E)-methyl 3-(2,3-dihydroxypropoxy)-4-(4-methoxybenzyloxy)but-2-enoate

: 1426310-22-6
(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-methoxy-2-oxoethyl)-2-((4-methoxybenzyloxy)methyl)tetrahydrofuran-3-yl hexanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -30 °C

2.1: camphor-10-sulfonic acid / dichloromethane; methanol / 1.5 h / 0 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

3.2: 3 h / -78 - 0 °C

4.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux

5.1: dmap; triethylamine / dichloromethane / 5.5 h / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; benzene; 3.1: |Swern Oxidation;
DOI:10.1021/ol4001894

Reference yield:

: 1426310-13-5
(R,E)-methyl 3-(2,3-bis(tert-butyldimethylsilyloxy)propoxy)-4-(4-methoxybenzyloxy)but-2-enoate

: 1426310-22-6
(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-methoxy-2-oxoethyl)-2-((4-methoxybenzyloxy)methyl)tetrahydrofuran-3-yl hexanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: camphor-10-sulfonic acid / dichloromethane; methanol / 1.5 h / 0 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

2.2: 3 h / -78 - 0 °C

3.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux

4.1: dmap; triethylamine / dichloromethane / 5.5 h / 0 - 20 °C

With dmap; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; benzene; 2.1: |Swern Oxidation;
DOI:10.1021/ol4001894