methyl 2-((2R,3R,4R)-4-(tertbutyldimethylsilyloxy)-3-hydroxy-2-((4-methoxybenzyloxy)methyl)-tetrahydrofuran-2-yl)acetate

Base Information

Chemical Name:methyl 2-((2R,3R,4R)-4-(tertbutyldimethylsilyloxy)-3-hydroxy-2-((4-methoxybenzyloxy)methyl)-tetrahydrofuran-2-yl)acetate
CAS No.:1426310-18-0
Molecular Formula:C₂₂H₃₆O₇Si
Molecular Weight:440.609
Hs Code.:

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

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Chemical Property of methyl 2-((2R,3R,4R)-4-(tertbutyldimethylsilyloxy)-3-hydroxy-2-((4-methoxybenzyloxy)methyl)-tetrahydrofuran-2-yl)acetate

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Technology Process of methyl 2-((2R,3R,4R)-4-(tertbutyldimethylsilyloxy)-3-hydroxy-2-((4-methoxybenzyloxy)methyl)-tetrahydrofuran-2-yl)acetate

There total 8 articles about methyl 2-((2R,3R,4R)-4-(tertbutyldimethylsilyloxy)-3-hydroxy-2-((4-methoxybenzyloxy)methyl)-tetrahydrofuran-2-yl)acetate 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: 19.0%

: 1426310-16-8
(R,E)-methyl 3-(2-(tert-butyldimethylsilyloxy)-3-oxopropoxy)-4-(4-methoxybenzyloxy)but-2-enoate

: 1426310-14-6
(S,E)-methyl 3-(2-(tert-butyldimethylsilyloxy)-3-hydroxypropoxy)-4-(4-methoxybenzyloxy)but-2-enoate

: 1426310-17-9
(3aR,6R,6aS)-6-(tert-butyldimethylsilyloxy)-3a-((4-methoxybenzyloxy)methyl)tetrahydrofuro[3,2-b]furan-2(5H)-one

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

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 2h; Concentration; Inert atmosphere; Reflux;
DOI:10.1021/ol4001894

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With 2,6-dimethylpyridine; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tri-n-butyl-tin hydride; dimethyl sulfoxide; 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

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

Guidance literature:: Multi-step reaction with 3 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

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