(E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester

Base Information

Chemical Name:(E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester
CAS No.:194283-82-4
Molecular Formula:C₂₁H₃₂O₆Si
Molecular Weight:408.567
Hs Code.:

Synonyms:(E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester

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Chemical Property of (E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester

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Technology Process of (E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester

There total 9 articles about (E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester 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: 100.0%

: 194283-79-9
(E)-3-[(1S,2S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-propoxy]-acrylic acid methyl ester

: 194283-82-4
(E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/jo9702812

Reference yield:

: 84379-53-3
2-O-benzyl-3,4-O-isopropylidene-L-threitol

: 194283-82-4
(E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

2: 86 percent / PTSA / methanol; H₂O / Ambient temperature

3: 95 percent / imidazole / CH₂Cl₂ / 4 h / Ambient temperature

4: 91 percent / N-methyl morpholine / CH₂Cl₂ / 10 h / Ambient temperature

5: 52 percent / Et₃N / methanol; H₂O / 42 h / 0 °C

6: 100 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 20 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; water;
DOI:10.1021/jo9702812

Reference yield:

: 21154-16-5,35572-31-7,89015-57-6,141042-56-0
diethyl-2,3-O-benzylidene-D-tartrate

: 194283-82-4
(E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / LiAlH₄ / diethyl ether; CH₂Cl₂ / 1.) room temperature, 1 h, 2.) reflux, 4 h

2: 70 percent / PTSA, MS 4A / CH₂Cl₂ / 7 h / Heating

3: 95 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

4: 86 percent / PTSA / methanol; H₂O / Ambient temperature

5: 95 percent / imidazole / CH₂Cl₂ / 4 h / Ambient temperature

6: 91 percent / N-methyl morpholine / CH₂Cl₂ / 10 h / Ambient temperature

7: 52 percent / Et₃N / methanol; H₂O / 42 h / 0 °C

8: 100 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 20 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane; water;
DOI:10.1021/jo9702812