(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethane-1,2-diol

Base Information

Chemical Name:(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethane-1,2-diol
CAS No.:155300-02-0
Molecular Formula:C₁₇H₂₆O₄
Molecular Weight:294.391
Hs Code.:

Synonyms:(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethane-1,2-diol

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Chemical Property of (1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethane-1,2-diol

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Technology Process of (1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethane-1,2-diol

There total 1 articles about (1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethane-1,2-diol 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: 93.0%

: 155300-01-9
{(2S,3S)-3-[(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl]-oxiranyl}-methanol

: 155300-02-0
(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethane-1,2-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 60 ℃;
DOI:10.1016/S0040-4039(00)76542-7

Reference yield:

: 155300-02-0
(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethane-1,2-diol

: 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

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) Bu₂SnO, 2.) Et₃N / 1.) MeOH, reflux, 45 min, 2.) MeOH, r.t., 15 min

2: 92 percent / LiEt₃BH / tetrahydrofuran / 6 h / Ambient temperature

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

4: 95 percent / H₂ / 10percent Pd/C / methanol / 16 h

5: 93 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂

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

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; potassium hydride; di(n-butyl)tin oxide; lithium triethylborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1039/a804170i

Reference yield:

: 155300-02-0
(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethane-1,2-diol

: 155846-45-0
{(E)-(1S,4S)-1-((R)-4-Benzyloxy-3-methyl-butyl)-4-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-pent-2-enyloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) Bu₂SnO, 2.) Et₃N / 1.) MeOH, reflux, 45 min, 2.) MeOH, r.t., 15 min

2: 92 percent / LiEt₃BH / tetrahydrofuran / 6 h / Ambient temperature

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

4: 95 percent / H₂ / 10percent Pd/C / methanol / 16 h

5: 93 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂

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

7: 63 percent / LiAlH₄, S-BINAL-H / tetrahydrofuran; methanol / 16 h / -100 °C

8: 98 percent / imidazole / dimethylformamide / 16 h

With 1H-imidazole; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; (S)-BINAL-H; 4 A molecular sieve; hydrogen; potassium hydride; di(n-butyl)tin oxide; lithium triethylborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/a804170i