(R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-[(1S,2R)-2-((1E,6Z)-(3R,4S)-3,4-dihydroxy-dodeca-1,6-dienyl)-cyclopropyl]-pentanoic acid methyl ester

Base Information

Chemical Name:(R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-[(1S,2R)-2-((1E,6Z)-(3R,4S)-3,4-dihydroxy-dodeca-1,6-dienyl)-cyclopropyl]-pentanoic acid methyl ester
CAS No.:183610-92-6
Molecular Formula:C₃₇H₅₄O₅Si
Molecular Weight:606.918
Hs Code.:

Synonyms:(R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-[(1S,2R)-2-((1E,6Z)-(3R,4S)-3,4-dihydroxy-dodeca-1,6-dienyl)-cyclopropyl]-pentanoic acid methyl ester

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Chemical Property of (R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-[(1S,2R)-2-((1E,6Z)-(3R,4S)-3,4-dihydroxy-dodeca-1,6-dienyl)-cyclopropyl]-pentanoic acid methyl ester

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Technology Process of (R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-[(1S,2R)-2-((1E,6Z)-(3R,4S)-3,4-dihydroxy-dodeca-1,6-dienyl)-cyclopropyl]-pentanoic acid methyl ester

There total 25 articles about (R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-[(1S,2R)-2-((1E,6Z)-(3R,4S)-3,4-dihydroxy-dodeca-1,6-dienyl)-cyclopropyl]-pentanoic 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: 77.0%

: 205808-82-8
(R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-((1S,2R)-2-{(E)-2-[(4R,5S)-2,2-dimethyl-5-((Z)-oct-2-enyl)-[1,3]dioxolan-4-yl]-vinyl}-cyclopropyl)-pentanoic acid methyl ester

: 183610-92-6
(R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-[(1S,2R)-2-((1E,6Z)-(3R,4S)-3,4-dihydroxy-dodeca-1,6-dienyl)-cyclopropyl]-pentanoic acid methyl ester

Guidance literature:: With acetic acid; In water; for 12h; Ambient temperature;
DOI:10.3987/com-97-s(n)58

Reference yield:

: 183610-97-1
Biphenyl-4-carboxylic acid (2S,3R)-3-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-oxiranylmethyl ester

: 183610-92-6
(R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-[(1S,2R)-2-((1E,6Z)-(3R,4S)-3,4-dihydroxy-dodeca-1,6-dienyl)-cyclopropyl]-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 98 percent / K₂CO₃ / methanol / 0.5 h / Ambient temperature

2: 97 percent / DMAP / CH₂Cl₂ / 2 h / 0 °C

3: 83 percent / 1.) BuLi / tetrahydrofuran / 1.) -78 deg C, 30 min.; 2.) -78 deg C -> room temp. over 5 h, then 1 h

4: 96 percent / dimethylformamide / 4 h / Ambient temperature

5: 92 percent / SmI₂, HMPA / tetrahydrofuran / 0.5 h / Ambient temperature

6: O₃, Me₂S / CH₂Cl₂; methanol / -78 deg C, then -> room temp., 2 h, then room temp., 8 h

7: K₂CO₃ / methanol / 16 h / 50 °C

8: 92 percent / NaBH₄ / methanol / 0.5 h / 0 °C

9: 99 percent / Bu₃P, pyridine / 3 h / 0 °C

10: 99 percent / m-CPBA / CH₂Cl₂ / 1 h / 0 °C

11: 80 percent / 1.) BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h; 2.) -78 deg C, 1 h then -> room temp., 1 h, then room temp., 1 h

12: 70 percent / pyridine / 12 h / Ambient temperature

13: 56 percent / Na₂HPO₄, 5percent Na-Hg / methanol; tetrahydrofuran / 1 h / 0 °C

14: 85 percent / AcOH / H₂O; tetrahydrofuran / 1 h / Ambient temperature

15: powdered molecular sieves 4A, PDC / CH₂Cl₂ / 2 h / Ambient temperature

16: NaH₂PO₄, NaClO₂, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.5 h / 0 °C

17: diethyl ether / 0 °C

18: 77 percent / AcOH / H₂O / 12 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; dipyridinium dichromate; n-butyllithium; samarium diiodide; sodium amalgam; 2-methyl-but-2-ene; dimethylsulfide; tributylphosphine; 4 A molecular sieve; potassium carbonate; ozone; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.3987/com-97-s(n)58

Reference yield:

: 121352-74-7
(2Z)-7-[(tert-butyldimethylsilyl)oxy]hept-2-en-1-ol

: 183610-92-6
(R)-5-(tert-Butyl-diphenyl-silanyloxy)-5-[(1S,2R)-2-((1E,6Z)-(3R,4S)-3,4-dihydroxy-dodeca-1,6-dienyl)-cyclopropyl]-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 1.) powdered 4A molecular sieves, D-(-)-diethyl tartrate, Ti(i-PrO)4; 2.) tert-butyl hyperoxide / CH₂Cl₂ / 1.) 0 deg C; 2.) -20 deg C, 20 h

2: 97 percent / DMAP / CH₂Cl₂ / 2 h / 0 °C

3: 83 percent / 1.) BuLi / tetrahydrofuran / 1.) -78 deg C, 30 min.; 2.) -78 deg C -> room temp. over 5 h, then 1 h

4: 96 percent / dimethylformamide / 4 h / Ambient temperature

5: 92 percent / SmI₂, HMPA / tetrahydrofuran / 0.5 h / Ambient temperature

6: O₃, Me₂S / CH₂Cl₂; methanol / -78 deg C, then -> room temp., 2 h, then room temp., 8 h

7: K₂CO₃ / methanol / 16 h / 50 °C

8: 92 percent / NaBH₄ / methanol / 0.5 h / 0 °C

9: 99 percent / Bu₃P, pyridine / 3 h / 0 °C

10: 99 percent / m-CPBA / CH₂Cl₂ / 1 h / 0 °C

11: 80 percent / 1.) BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h; 2.) -78 deg C, 1 h then -> room temp., 1 h, then room temp., 1 h

12: 70 percent / pyridine / 12 h / Ambient temperature

13: 56 percent / Na₂HPO₄, 5percent Na-Hg / methanol; tetrahydrofuran / 1 h / 0 °C

14: 85 percent / AcOH / H₂O; tetrahydrofuran / 1 h / Ambient temperature

15: powdered molecular sieves 4A, PDC / CH₂Cl₂ / 2 h / Ambient temperature

16: NaH₂PO₄, NaClO₂, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.5 h / 0 °C

17: diethyl ether / 0 °C

18: 77 percent / AcOH / H₂O / 12 h / Ambient temperature

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; dipyridinium dichromate; n-butyllithium; samarium diiodide; sodium amalgam; 2-methyl-but-2-ene; dimethylsulfide; diethyl (2S,3S)-tartrate; tributylphosphine; 4 A molecular sieve; potassium carbonate; ozone; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.3987/com-97-s(n)58