(4R)-4-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-6-vinyl-1,3-dioxan-2-one

Base Information

Chemical Name:(4R)-4-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-6-vinyl-1,3-dioxan-2-one
CAS No.:950588-62-2
Molecular Formula:C₂₆H₃₂O₄Si
Molecular Weight:436.623
Hs Code.:

Synonyms:(4R)-4-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-6-vinyl-1,3-dioxan-2-one

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Chemical Property of (4R)-4-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-6-vinyl-1,3-dioxan-2-one

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Technology Process of (4R)-4-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-6-vinyl-1,3-dioxan-2-one

There total 8 articles about (4R)-4-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-6-vinyl-1,3-dioxan-2-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: 98.0%

: 950588-61-1
(5R)-5-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-5-hydroxypent-1-en-3-ol

: 32315-10-9
bis(trichloromethyl) carbonate

: 950588-62-2
(4R)-4-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-6-vinyl-1,3-dioxan-2-one

Guidance literature:: With pyridine; triethylamine; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo800335g

Reference yield:

: 950588-56-4
(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxyhex-4-enoic acid N-methoxy-N-methylamide

: 950588-62-2
(4R)-4-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-6-vinyl-1,3-dioxan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / diethylzinc / CH₂Cl₂; hexane / 3 h / -15 - 20 °C

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 °C

3: DIBAL-H / tetrahydrofuran / 0.25 h / -78 °C

4: 85 percent / tetrahydrofuran / 0.83 h / -78 °C

5: acetic acid / tetrahydrofuran; H₂O / 1 h / 20 °C

6: pyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; 2,6-dimethylpyridine; 4 A molecular sieve; diethylzinc; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; hexane; dichloromethane; water; 1: Simmons-Smith cyclopropanation;
DOI:10.1021/ol701564x

Reference yield:

: 950588-55-3
(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one

: 950588-62-2
(4R)-4-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-6-vinyl-1,3-dioxan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 71 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

2: 97 percent / diethylzinc / CH₂Cl₂; hexane / 3 h / -15 - 20 °C

3: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 °C

4: DIBAL-H / tetrahydrofuran / 0.25 h / -78 °C

5: 85 percent / tetrahydrofuran / 0.83 h / -78 °C

6: acetic acid / tetrahydrofuran; H₂O / 1 h / 20 °C

7: pyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 4 A molecular sieve; diethylzinc; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; hexane; dichloromethane; water; 2: Simmons-Smith cyclopropanation;
DOI:10.1021/ol701564x