(S)-1-{(2R,5S,7R,8S)-2-Butyl-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-2-yl}-ethane-1,2-diol

Base Information

• Chemical Name: (S)-1-{(2R,5S,7R,8S)-2-Butyl-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-2-yl}-ethane-1,2-diol
• CAS No.: 250379-11-4
• Molecular Formula: C₂₅H₄₀O₆
• Molecular Weight: 436.589
• Mol file: 250379-11-4.mol

Synonyms:(S)-1-{(2R,5S,7R,8S)-2-Butyl-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-2-yl}-ethane-1,2-diol

Chemical Property of (S)-1-{(2R,5S,7R,8S)-2-Butyl-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-2-yl}-ethane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-{(2R,5S,7R,8S)-2-Butyl-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-2-yl}-ethane-1,2-diol

There total 21 articles about (S)-1-{(2R,5S,7R,8S)-2-Butyl-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-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: 86.0%

C41H58O6Si (250379-10-3) → (S)-1-{(2R,5S,7R,8S)-2-Butyl-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-2-yl}-ethane-1,2-diol (250379-11-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol990884v

Reference yield:

1-(tetrahydropyranyloxy)-4-pentyn (62992-46-5) → (S)-1-{(2R,5S,7R,8S)-2-Butyl-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-2-yl}-ethane-1,2-diol (250379-11-4)

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: 1.) p-TsOH / 1.) CHCl₃, r.t., 2.) CHCl₃, r.t.

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; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(96)01460-8

Reference yield:

6-tetrahydropyranyloxy-2-hexyn-1-ol (66084-35-3) → (S)-1-{(2R,5S,7R,8S)-2-Butyl-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-2-yl}-ethane-1,2-diol (250379-11-4)

Guidance literature:

Multi-step reaction with 14 steps

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

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

3: 92 percent / t-BuOOH, (+)-DEPT, Ti(Oi-Pr)4, 4A-MS / CH₂Cl₂ / -23 °C

4: AcOH / tetrahydrofuran; H₂O / Ambient temperature

5: p-TsOH / CH₂Cl₂ / Ambient temperature

6: 92 percent / RuCl₃, NaIO₄ / acetonitrile; CCl₄; H₂O / Ambient temperature

7: Me₂AlCl / CH₂Cl₂ / Ambient temperature

8: PPTS / CH₂Cl₂ / Ambient temperature

9: Ac₂O / Ambient temperature

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

11: 97 percent / H₂ / Pd/C / ethyl acetate / Ambient temperature

12: 34 percent / PPTS / methanol / Ambient temperature

13: 80 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

14: 1.) p-TsOH / 1.) CHCl₃, r.t., 2.) CHCl₃, r.t.

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; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(96)01460-8

upstream raw materials:

(3R,4S)-6-((1S,2R,5S)-2-Butyl-2-methylsulfanylmethoxy-6,8-dioxa-bicyclo[3.2.1]oct-5-yl)-1-(4-methoxy-benzyloxy)-4-methyl-hexan-3-ol

C₄₁H₅₈O₆Si

C₅₅H₉₂O₇SSi₃

1-(tetrahydropyranyloxy)-4-pentyn

Downstream raw materials:

C₃₁H₅₄O₆Si

C₃₂H₄₆O₉

C₃₂H₄₈O₉

C₃₈H₆₂O₉Si