(3E,1''S,2S,2'R,3'S,5S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-ol

Base Information

Chemical Name:(3E,1''S,2S,2'R,3'S,5S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-ol
CAS No.:155846-44-9
Molecular Formula:C₂₅H₄₀O₄
Molecular Weight:404.59
Hs Code.:

Synonyms:(3E,1''S,2S,2'R,3'S,5S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-ol

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Chemical Property of (3E,1''S,2S,2'R,3'S,5S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-ol

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Technology Process of (3E,1''S,2S,2'R,3'S,5S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-ol

There total 16 articles about (3E,1''S,2S,2'R,3'S,5S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-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: 63.0%

: 155846-43-8
(3E,1''S,2S,2'R,3'S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-one

: 155846-44-9
(3E,1''S,2S,2'R,3'S,5S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-ol

Guidance literature:: With lithium aluminium tetrahydride; (S)-BINAL-H; In tetrahydrofuran; methanol; at -100 ℃; for 16h;
DOI:10.1039/a804170i

Reference yield:

: 155846-43-8
(3E,1''S,2S,2'R,3'S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-one

: (E)-(2S,5R,8R)-9-Benzyloxy-2-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-8-methyl-non-3-en-5-ol

: 155846-44-9
(3E,1''S,2S,2'R,3'S,5S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-ol

Guidance literature:: With (-)-(S)-BINAL-H; In tetrahydrofuran; at -100 ℃; Yield given. Yields of byproduct given;
DOI:10.1016/S0040-4039(00)76543-9

Reference yield:

: 155300-04-2
(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethanol

: 155846-44-9
(3E,1''S,2S,2'R,3'S,5S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / KH / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 3 h

2: 95 percent / H₂ / 10percent Pd/C / methanol / 16 h

3: 93 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂

4: 1.) LiCl, 2.) diisopropylethylamine / 1.) MeCN, 10 min, 2.) MeCN, 16 h

5: 63 percent / LiAlH₄, S-BINAL-H / tetrahydrofuran; methanol / 16 h / -100 °C

With lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; (S)-BINAL-H; 4 A molecular sieve; hydrogen; potassium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1039/a804170i