(E)-(1R,4R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-ol

Base Information

Chemical Name:(E)-(1R,4R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-ol
CAS No.:876911-51-2
Molecular Formula:C₃₉H₆₈O₅Si₂
Molecular Weight:673.137
Hs Code.:

(E)-(1R,4R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-ol

Synonyms:(E)-(1R,4R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-ol

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Chemical Property of (E)-(1R,4R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-ol

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Technology Process of (E)-(1R,4R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-ol

There total 14 articles about (E)-(1R,4R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-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: 83.0%

: 876911-42-1
(E)-(R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-one

: 876911-51-2
(E)-(1R,4R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-ol

Guidance literature:: With B-chlorodiisopinocampheylborane; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1021/jo051889a

Reference yield:

: 876911-27-2
((E)-10-Chloro-dec-8-en-5-ynyloxymethyl)-benzene

: 876911-51-2
(E)-(1R,4R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: CH₃MgCl / tetrahydrofuran / 3 h / 50 - 60 °C

1.2: 86 percent / CuCl / tetrahydrofuran / 3 h / Heating

2.1: 92 percent / PPTS / ethanol / 6 h / 55 °C

3.1: 60 percent / LiAlH₄ / tetrahydrofuran / 24 h / Heating

4.1: 72 percent / titanium(IV) isopropoxide; (-)-diethyl D-tartrate; tert-butyl hydroperoxide / CH₂Cl₂ / 15 h / -30 - -20 °C

5.1: 95 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

6.1: 92 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C

7.1: 65 percent / K₂CO₃ / methanol / 4 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -20 - -10 °C

8.2: 70 percent / tetrahydrofuran / -20 - 20 °C

9.1: 99 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

10.1: 78 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C

11.1: 90 percent / NaIO₄; SiO₂ / CH₂Cl₂; H₂O / 12 h / 20 °C

12.1: NaH / tetrahydrofuran; various solvent(s) / 1 h / 0 - 20 °C

12.2: 90 percent / tetrahydrofuran / 0.25 h / 20 °C

13.1: 83 percent / (+)-DIP-Cl / tetrahydrofuran / -78 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; AD-mix-α; lithium aluminium tetrahydride; n-butyllithium; diethyl (2S,3S)-tartrate; methanesulfonamide; methylmagnesium chloride; pyridinium p-toluenesulfonate; silica gel; sodium hydride; potassium carbonate; triethylamine; B-chlorodiisopinocampheylborane; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; tert-butyl alcohol; 4.1: Sharpless asymmetric epoxidation / 6.1: Sharpless asymmetric dihydroxylation / 12.2: Horner-Emmons condensation;
DOI:10.1021/jo051889a

Reference yield:

: 876911-30-7
(2E,5E)-13-Benzyloxy-trideca-2,5-dien-8-yn-1-ol

: 876911-51-2
(E)-(1R,4R)-1-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-non-2-en-4-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 72 percent / titanium(IV) isopropoxide; (-)-diethyl D-tartrate; tert-butyl hydroperoxide / CH₂Cl₂ / 15 h / -30 - -20 °C

2.1: 95 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

3.1: 92 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C

4.1: 65 percent / K₂CO₃ / methanol / 4 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -20 - -10 °C

5.2: 70 percent / tetrahydrofuran / -20 - 20 °C

6.1: 99 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

7.1: 78 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C

8.1: 90 percent / NaIO₄; SiO₂ / CH₂Cl₂; H₂O / 12 h / 20 °C

9.1: NaH / tetrahydrofuran; various solvent(s) / 1 h / 0 - 20 °C

9.2: 90 percent / tetrahydrofuran / 0.25 h / 20 °C

10.1: 83 percent / (+)-DIP-Cl / tetrahydrofuran / -78 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; AD-mix-α; n-butyllithium; diethyl (2S,3S)-tartrate; methanesulfonamide; silica gel; sodium hydride; potassium carbonate; triethylamine; B-chlorodiisopinocampheylborane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; tert-butyl alcohol; 1.1: Sharpless asymmetric epoxidation / 3.1: Sharpless asymmetric dihydroxylation / 9.2: Horner-Emmons condensation;
DOI:10.1021/jo051889a