(4S,5S)-Z,Z-4-[10-(tert-butyldiphenylsilyloxy)decyl]-5-(3,7-eicosadienyl)-2,2-dimethyl-1,3-dioxolane

Base Information

Chemical Name:(4S,5S)-Z,Z-4-[10-(tert-butyldiphenylsilyloxy)decyl]-5-(3,7-eicosadienyl)-2,2-dimethyl-1,3-dioxolane
CAS No.:332095-66-6
Molecular Formula:C₅₁H₈₄O₃Si
Molecular Weight:773.312
Hs Code.:

Synonyms:(4S,5S)-Z,Z-4-[10-(tert-butyldiphenylsilyloxy)decyl]-5-(3,7-eicosadienyl)-2,2-dimethyl-1,3-dioxolane

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Chemical Property of (4S,5S)-Z,Z-4-[10-(tert-butyldiphenylsilyloxy)decyl]-5-(3,7-eicosadienyl)-2,2-dimethyl-1,3-dioxolane

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Technology Process of (4S,5S)-Z,Z-4-[10-(tert-butyldiphenylsilyloxy)decyl]-5-(3,7-eicosadienyl)-2,2-dimethyl-1,3-dioxolane

There total 13 articles about (4S,5S)-Z,Z-4-[10-(tert-butyldiphenylsilyloxy)decyl]-5-(3,7-eicosadienyl)-2,2-dimethyl-1,3-dioxolane 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: 64.0%

: 332095-58-6
Z,Z-1-iodo-1,5-octadecadiene

: 332095-64-4
(4S,5S)-4-[10-(tert-butyldiphenylsilyloxy)decyl]-2,2-dimethyl-5-(2-iodoethyl)-1,3-dioxolane

: 332095-66-6
(4S,5S)-Z,Z-4-[10-(tert-butyldiphenylsilyloxy)decyl]-5-(3,7-eicosadienyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Z,Z-1-iodo-1,5-octadecadiene; With tert.-butyl lithium; In diethyl ether; at -50 ℃; for 0.5h;

(4S,5S)-4-[10-(tert-butyldiphenylsilyloxy)decyl]-2,2-dimethyl-5-(2-iodoethyl)-1,3-dioxolane; In tetrahydrofuran; diethyl ether; at 20 ℃; for 4h; Further stages.;
DOI:10.1039/b002905j

Reference yield:

: 332095-61-1
methyl E-14-(tert-butyldiphenylsilyloxy)-3-tetradecenoate

: 332095-66-6
(4S,5S)-Z,Z-4-[10-(tert-butyldiphenylsilyloxy)decyl]-5-(3,7-eicosadienyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 68 percent / K3Fe(CN)6; K2CO3; methanesulfoneamide / α-1,4-bis(dihydroquininyl)phthalazine; K2OsO4 / methanol; 2-methyl-propan-2-ol / 96 h / 0 °C

2.1: 98 percent / LiAlH₄ / tetrahydrofuran / -78 - 20 °C

3.1: Amberlyst 15 ion exchange resin / acetone / 2 h / 20 °C

4.1: triphenylphosphine; imidazole; I₂ / tetrahydrofuran / 0.25 h / 0 - 20 °C

5.1: t-BuLi

5.2: MgBr₂; NiCl₂(PPh₃)4

With 1H-imidazole; lithium aluminium tetrahydride; methanesulfonamide; iodine; tert.-butyl lithium; potassium carbonate; triphenylphosphine; potassium hexacyanoferrate(III); potassium osmate(VI); α-1,4-bis(dihydroquininyl)phthalazine; Amberlyst 15 ion exchange resin; In tetrahydrofuran; methanol; acetone; tert-butyl alcohol; 3.1: Meyer Reaction;
DOI:10.1039/b002905j

Reference yield:

: 332095-60-0
(4S,5S)-5-[10-(tert-butyldiphenylsilyloxy)decyl]-4,5-dihydro-4-hydroxy-2(3H)-furanone

: 332095-66-6
(4S,5S)-Z,Z-4-[10-(tert-butyldiphenylsilyloxy)decyl]-5-(3,7-eicosadienyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / LiAlH₄ / tetrahydrofuran / -78 - 20 °C

2.1: Amberlyst 15 ion exchange resin / acetone / 2 h / 20 °C

3.1: triphenylphosphine; imidazole; I₂ / tetrahydrofuran / 0.25 h / 0 - 20 °C

4.1: t-BuLi

4.2: MgBr₂; NiCl₂(PPh₃)4

With 1H-imidazole; lithium aluminium tetrahydride; iodine; tert.-butyl lithium; triphenylphosphine; Amberlyst 15 ion exchange resin; In tetrahydrofuran; acetone; 2.1: Meyer Reaction;
DOI:10.1039/b002905j