(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol

Base Information

Chemical Name:(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol
CAS No.:412342-85-9
Molecular Formula:C₃₈H₆₉IO₅Si₂
Molecular Weight:789.038
Hs Code.:

(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol

Synonyms:(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol

Suppliers and Price of (E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol

There total 18 articles about (E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-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: 87.0%

: 412342-84-8
(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-enoic acid ethyl ester

: 412342-85-9
(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.5h;
DOI:10.1021/ol017266a

Reference yield:

: (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-hex-5-en-3-ol

: 412342-85-9
(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol

Guidance literature:: Multi-step reaction with 18 steps

1.1: 92 percent / TfOH / CH₂Cl₂ / 3.5 h / 20 °C

2.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 0 - 20 °C

2.2: 27.5percent H₂O₂; 2N NaOH / methanol / 2 h / 0 °C

3.1: PDC / dimethylformamide / 48 h / 20 °C

4.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

5.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

5.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

6.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

7.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

8.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

9.1: imidazole / dimethylformamide / 1.5 h / 0 °C

10.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -50 °C

11.1: aq. HF / tetrahydrofuran; acetonitrile / 1.5 h / 20 °C

12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

13.1: (n-Bu)2BOTf; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

13.2: CH₂Cl₂ / -78 - 20 °C

14.1: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -50 - 20 °C

15.1: 82 percent / LiBH₄ / diethyl ether; H₂O / 1.5 h / 20 °C

16.1: 81 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.17 h / 20 °C

17.1: 90 percent / toluene / 5 h / Heating

18.1: 87 percent / i-Bu₂AlH / toluene / 0.5 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; dipyridinium dichromate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; trifluorormethanesulfonic acid; 4 A molecular sieve; Li(Pr-i)2; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 13.2: Evans aldol addition / 17.1: Wittig reaction;
DOI:10.1021/ol017266a

Reference yield:

: 412342-77-9
((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane

: 412342-85-9
(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol

Guidance literature:: Multi-step reaction with 17 steps

1.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 0 - 20 °C

1.2: 27.5percent H₂O₂; 2N NaOH / methanol / 2 h / 0 °C

2.1: PDC / dimethylformamide / 48 h / 20 °C

3.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

4.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

4.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

5.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

6.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

7.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

8.1: imidazole / dimethylformamide / 1.5 h / 0 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -50 °C

10.1: aq. HF / tetrahydrofuran; acetonitrile / 1.5 h / 20 °C

11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

12.1: (n-Bu)2BOTf; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

12.2: CH₂Cl₂ / -78 - 20 °C

13.1: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -50 - 20 °C

14.1: 82 percent / LiBH₄ / diethyl ether; H₂O / 1.5 h / 20 °C

15.1: 81 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.17 h / 20 °C

16.1: 90 percent / toluene / 5 h / Heating

17.1: 87 percent / i-Bu₂AlH / toluene / 0.5 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; dipyridinium dichromate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; Li(Pr-i)2; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 12.2: Evans aldol addition / 16.1: Wittig reaction;
DOI:10.1021/ol017266a