(5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(methoxycarbonyl)furan-2(5H)-one

Base Information

Chemical Name:(5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(methoxycarbonyl)furan-2(5H)-one
CAS No.:1361049-72-0
Molecular Formula:C₂₃H₃₂O₆Si
Molecular Weight:432.589
Hs Code.:

Synonyms:(5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(methoxycarbonyl)furan-2(5H)-one

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Chemical Property of (5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(methoxycarbonyl)furan-2(5H)-one

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Technology Process of (5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(methoxycarbonyl)furan-2(5H)-one

There total 6 articles about (5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(methoxycarbonyl)furan-2(5H)-one 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: 67.0%

: 1361049-71-9
C₁₆H₂₆O₆Si

: 100-39-0
benzyl bromide

: 1361049-72-0
(5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(methoxycarbonyl)furan-2(5H)-one

Guidance literature:: C₁₆H₂₆O₆Si; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 21h;
DOI:10.1002/anie.201106889

Reference yield:

: 1361049-70-8
methyl (5R)-5-hydroxy-3-oxo-6-heptenoate

: 1361049-72-0
(5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(methoxycarbonyl)furan-2(5H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 44 h / -35 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 4 h / -78 °C

3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 19 h / -78 - 20 °C

3.3: 21 h / -78 - 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

4.2: 21 h / 20 °C

With 2,6-dimethylpyridine; sodium hydride; acetic acid; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1002/anie.201106889

Reference yield:

: 521315-88-8
methyl (3R,5R)-3,5-dihydroxy-6-heptenoate

: 1361049-72-0
(5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(methoxycarbonyl)furan-2(5H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 4 h / -78 °C

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 19 h / -78 - 20 °C

2.3: 21 h / -78 - 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

3.2: 21 h / 20 °C

With 2,6-dimethylpyridine; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/anie.201106889