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

Base Information

Chemical Name:(5R)-5-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-5-hydroxypent-1-en-3-ol
CAS No.:950588-61-1
Molecular Formula:C₂₅H₃₄O₃Si
Molecular Weight:410.629
Hs Code.:

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

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Chemical Property of (5R)-5-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-5-hydroxypent-1-en-3-ol

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Technology Process of (5R)-5-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-5-hydroxypent-1-en-3-ol

There total 7 articles about (5R)-5-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-5-hydroxypent-1-en-3-ol 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:

: 950588-60-0
(5R)-5-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-5-(triethylsilanyloxy)pent-1-en-3-ol

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

Guidance literature:: With acetic acid; In tetrahydrofuran; water; at 20 ℃; for 1h;
DOI:10.1021/ol701564x

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With 2,6-dimethylpyridine; 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

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

Guidance literature:: Multi-step reaction with 6 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

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