(2E,6E)-(R)-8-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dien-1-ol

Base Information

Chemical Name:(2E,6E)-(R)-8-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dien-1-ol
CAS No.:82431-66-1
Molecular Formula:C₃₇H₅₄O₄Si
Molecular Weight:590.919
Hs Code.:

Synonyms:(2E,6E)-(R)-8-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dien-1-ol

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Chemical Property of (2E,6E)-(R)-8-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dien-1-ol

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Technology Process of (2E,6E)-(R)-8-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dien-1-ol

There total 19 articles about (2E,6E)-(R)-8-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dien-1-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:

: 112320-71-5
(2E,6E)-(R)-8-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dienoic acid ethyl ester

: 82431-66-1
(2E,6E)-(R)-8-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dien-1-ol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1021/jo00238a031

Reference yield:

: 128777-45-7
9(R)-hydroxy-1,1,3-trimethoxy-8(S)-methyldec-3-en-5-one

: 82431-66-1
(2E,6E)-(R)-8-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dien-1-ol

Guidance literature:: Multi-step reaction with 13 steps

1: 35percent HClO₄ / CH₂Cl₂ / 0.08 h / Irradiation

2: 50 percent / 1.) 1IBu₃P>4 / 1.) ether, THF, from -55 deg C to -45 deg C, 45 min, 2.) 15 min

3: 74 percent / NaBH₄ / 1,2-dimethoxy-ethane / 3 h / 0 °C

4: 97 percent / DMAP, imidazole / dimethylformamide / 48 h

5: 1.) 9-BBN, 2.) NaOH, 30percent aq. H₂O₂ / 1.) THF, irradiation, 1 h, 2.) 4 h

6: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 5 min

7: CH₂Cl₂ / 5 h / Heating

8: Dibal-H / diethyl ether / 1 h / -78 °C

9: CBr₄, Ph₃P / acetonitrile / 0.25 h

11: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 5 min

12: CH₂Cl₂ / 2.5 h / Heating

13: Dibal-H / tetrahydrofuran; hexane / 0.5 h / -78 °C

With 1H-imidazole; dmap; sodium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; perchloric acid; oxalyl dichloride; tetrakiscopper(I); carbon tetrabromide; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00238a031

Reference yield:

: 82415-23-4
Dithiocarbonic acid S-[(E)-(R)-1-{(E)-2-[(2S,4S,6S,9S)-4-(tert-butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-vinyl}-1,3-dimethyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyl] ester S-methyl ester

: 82431-66-1
(2E,6E)-(R)-8-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dien-1-ol

: 82431-66-1,105087-29-4,105087-30-7
(2E,6E)-(R)-8-[(2R,4S,6R,8S,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dien-1-ol

Guidance literature:: With tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) 80 deg C, 2.) MeOH;
DOI:10.1021/ja00381a049