{(2S,3R,6S,8R,9S)-3-Butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-yl}-methanol

Base Information

Chemical Name:{(2S,3R,6S,8R,9S)-3-Butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-yl}-methanol
CAS No.:182284-89-5
Molecular Formula:C₂₇H₄₄O₆S
Molecular Weight:496.709
Hs Code.:

Synonyms:{(2S,3R,6S,8R,9S)-3-Butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-yl}-methanol

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Chemical Property of {(2S,3R,6S,8R,9S)-3-Butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-yl}-methanol

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Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of {(2S,3R,6S,8R,9S)-3-Butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-yl}-methanol

There total 25 articles about {(2S,3R,6S,8R,9S)-3-Butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-yl}-methanol 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:

: 1053617-67-6
tert-Butyl-{(2S,3R,6S,8R,9S)-3-butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethoxy}-diphenyl-silane

: 182284-89-5
{(2S,3R,6S,8R,9S)-3-Butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-yl}-methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol0060634

Reference yield:

: 250378-97-3
(S)-1-((R)-2-Butyl-tetrahydro-furan-2-yl)-ethane-1,2-diol

: 182284-89-5
{(2S,3R,6S,8R,9S)-3-Butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-yl}-methanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: imidazole; DMAP / dimethylformamide / 0 - 20 °C

2.1: dimethylformamide / 0 - 20 °C

3.1: 20 percent / RuCl₃; NaIO₄ / acetonitrile; CCl₄; aq. phosphate buffer / 20 °C / pH 8

4.1: Me₂AlCl / CH₂Cl₂ / 0 - 20 °C

4.2: TESCl; imidazole; DMAP / dimethylformamide / 0 - 20 °C

4.3: Ac₂O / 20 °C

5.1: n-BuLi / tetrahydrofuran / 0 - 20 °C

5.2: H₂ / Pd/C / ethyl acetate / 20 °C

6.1: 54 percent / CSA / CHCl₃; methanol / 0 - 20 °C

7.1: TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; ruthenium trichloride; sodium periodate; n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dimethylaluminum chloride; In tetrahydrofuran; methanol; tetrachloromethane; phosphate buffer; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile; 1.1: Addition / 2.1: Addition / 3.1: Substitution / 4.1: Addition / 4.2: Addition / 4.3: Addition / 5.1: Condensation / 5.2: Hydrogenation / 6.1: Cyclization / 7.1: desilylation;
DOI:10.1021/ol0060634

Reference yield:

: 62992-46-5
1-(tetrahydropyranyloxy)-4-pentyn

: 182284-89-5
{(2S,3R,6S,8R,9S)-3-Butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-yl}-methanol

Guidance literature:: Multi-step reaction with 15 steps

1: 90 percent / n-BuLi / tetrahydrofuran / Ambient temperature

2: 1.) LAH, NaOMe, 2.) I₂ / 1.) THF, reflux, 2.) -78 deg C to r.t.

3: 1.) n-Bu₂CuLi / 1.) Et₂O, -30 deg C, 2.) -30 deg C to r.t.

4: 92 percent / t-BuOOH, (+)-DEPT, Ti(Oi-Pr)4, 4A-MS / CH₂Cl₂ / -23 °C

5: AcOH / tetrahydrofuran; H₂O / Ambient temperature

6: p-TsOH / CH₂Cl₂ / Ambient temperature

7: 92 percent / RuCl₃, NaIO₄ / acetonitrile; CCl₄; H₂O / Ambient temperature

8: Me₂AlCl / CH₂Cl₂ / Ambient temperature

9: PPTS / CH₂Cl₂ / Ambient temperature

10: Ac₂O / Ambient temperature

11: 1.) n-BuLi / 1.) THF, -78 deg C, to r.t., 2.) 0 deg C to r.t.

12: 97 percent / H₂ / Pd/C / ethyl acetate / Ambient temperature

13: 34 percent / PPTS / methanol / Ambient temperature

14: 80 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

15: CDCl₃ / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium trichloride; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; (+)-DEPT; lithium di-n-butylcuprate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium methylate; dimethylaluminum chloride; pyridinium p-toluenesulfonate; acetic anhydride; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; chloroform-d1; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4039(96)01460-8