(3S,4R)-1-[(2R,5S,6R)-6(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-methyl-oct-6-yn-4-ol

Base Information

• Chemical Name: (3S,4R)-1-[(2R,5S,6R)-6(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-methyl-oct-6-yn-4-ol
• CAS No.: 872591-63-4
• Molecular Formula: C₃₃H₄₈O₄Si
• Molecular Weight: 536.827
• Mol file: 872591-63-4.mol

Synonyms:(3S,4R)-1-[(2R,5S,6R)-6(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-methyl-oct-6-yn-4-ol

Chemical Property of (3S,4R)-1-[(2R,5S,6R)-6(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-methyl-oct-6-yn-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-1-[(2R,5S,6R)-6(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-methyl-oct-6-yn-4-ol

There total 22 articles about (3S,4R)-1-[(2R,5S,6R)-6(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-methyl-oct-6-yn-4-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:

(2E)-4-(4-methoxybenzyloxy)-2-methylbut-2-enoic acid ethyl ester (167687-18-5) → (3S,4R)-1-[(2R,5S,6R)-6(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-methyl-oct-6-yn-4-ol (872591-63-4)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 92 percent / DIBAH / diethyl ether / 0.25 h / 20 °C

2.1: 84 percent / TBHP; (+)-DET; MS 4 Angstroem / Ti(O-iPr)4 / CH₂Cl₂ / 24 h / -25 °C

3.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / 1 h / -78 °C

4.1: benzene / 1 h / 20 °C

5.1: 96 percent / n-Bu₃P; HCO₂H; triethylamine / Pd₂(dba)3*CHCl₃ / dioxane / 5 h / 20 °C

6.1: 100 percent / imidazole / dimethylformamide / 4 h / 20 °C

7.1: NMO; OsO₄ / acetone; H₂O / 144 h / 20 °C

8.1: Pb(OAc)4 / toluene / 3 h / 20 °C

9.1: Ph₃P; triethylamine / CH₂Cl₂ / 24 h / 0 °C

10.1: imidazole / dimethylformamide / 24 h / 20 °C

11.1: 97 percent / n-BuLi / tetrahydrofuran / 2 h / -78 - 20 °C

12.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C

12.2: 87 percent / tetrahydrofuran / 3 h / 0 - 20 °C

13.1: 97 percent / PPTS / 4 h / 20 °C

14.1: 99 percent / pyridine / 2 h / 20 °C

15.1: 8.8 mg / DDQ / CH₂Cl₂; methanol / 4 h / 20 °C

16.1: 4.8 mg / potassium carbonate / methanol / 24 h / 20 °C

17.1: hydrogen / Pd/C / ethyl acetate / 120 h / 20 °C

17.2: 81 percent / PPTS / methanol / 1 h / 20 °C

18.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

18.2: BF₃*OEt / tetrahydrofuran / 1 h / -78 °C

With pyridine; 1H-imidazole; lead(IV) acetate; tert.-butylhydroperoxide; osmium(VIII) oxide; n-butyllithium; formic acid; N-methyl-2-indolinone; oxalyl dichloride; diethyl (2R,3R)-tartrate; tributylphosphine; MS 4 Angstroem; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; titanium(IV) isopropylate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ol052039k

Reference yield:

(2E)-4-[(4-methoxyphenyl)methoxy]-2-methylbut-2-en-1-ol (167687-19-6) → (3S,4R)-1-[(2R,5S,6R)-6(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-methyl-oct-6-yn-4-ol (872591-63-4)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 84 percent / TBHP; (+)-DET; MS 4 Angstroem / Ti(O-iPr)4 / CH₂Cl₂ / 24 h / -25 °C

2.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / 1 h / -78 °C

3.1: benzene / 1 h / 20 °C

4.1: 96 percent / n-Bu₃P; HCO₂H; triethylamine / Pd₂(dba)3*CHCl₃ / dioxane / 5 h / 20 °C

5.1: 100 percent / imidazole / dimethylformamide / 4 h / 20 °C

6.1: NMO; OsO₄ / acetone; H₂O / 144 h / 20 °C

7.1: Pb(OAc)4 / toluene / 3 h / 20 °C

8.1: Ph₃P; triethylamine / CH₂Cl₂ / 24 h / 0 °C

9.1: imidazole / dimethylformamide / 24 h / 20 °C

10.1: 97 percent / n-BuLi / tetrahydrofuran / 2 h / -78 - 20 °C

11.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C

11.2: 87 percent / tetrahydrofuran / 3 h / 0 - 20 °C

12.1: 97 percent / PPTS / 4 h / 20 °C

13.1: 99 percent / pyridine / 2 h / 20 °C

14.1: 8.8 mg / DDQ / CH₂Cl₂; methanol / 4 h / 20 °C

15.1: 4.8 mg / potassium carbonate / methanol / 24 h / 20 °C

16.1: hydrogen / Pd/C / ethyl acetate / 120 h / 20 °C

16.2: 81 percent / PPTS / methanol / 1 h / 20 °C

17.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

17.2: BF₃*OEt / tetrahydrofuran / 1 h / -78 °C

With pyridine; 1H-imidazole; lead(IV) acetate; tert.-butylhydroperoxide; osmium(VIII) oxide; n-butyllithium; formic acid; N-methyl-2-indolinone; oxalyl dichloride; diethyl (2R,3R)-tartrate; tributylphosphine; MS 4 Angstroem; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; titanium(IV) isopropylate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ol052039k

Reference yield:

[3-(4-methoxybenzyloxymethyl)-2-methyloxiranyl]methanol (167687-20-9) → (3S,4R)-1-[(2R,5S,6R)-6(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-methyl-oct-6-yn-4-ol (872591-63-4)

Guidance literature:

Multi-step reaction with 16 steps

1.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / 1 h / -78 °C

2.1: benzene / 1 h / 20 °C

3.1: 96 percent / n-Bu₃P; HCO₂H; triethylamine / Pd₂(dba)3*CHCl₃ / dioxane / 5 h / 20 °C

4.1: 100 percent / imidazole / dimethylformamide / 4 h / 20 °C

5.1: NMO; OsO₄ / acetone; H₂O / 144 h / 20 °C

6.1: Pb(OAc)4 / toluene / 3 h / 20 °C

7.1: Ph₃P; triethylamine / CH₂Cl₂ / 24 h / 0 °C

8.1: imidazole / dimethylformamide / 24 h / 20 °C

9.1: 97 percent / n-BuLi / tetrahydrofuran / 2 h / -78 - 20 °C

10.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C

10.2: 87 percent / tetrahydrofuran / 3 h / 0 - 20 °C

11.1: 97 percent / PPTS / 4 h / 20 °C

12.1: 99 percent / pyridine / 2 h / 20 °C

13.1: 8.8 mg / DDQ / CH₂Cl₂; methanol / 4 h / 20 °C

14.1: 4.8 mg / potassium carbonate / methanol / 24 h / 20 °C

15.1: hydrogen / Pd/C / ethyl acetate / 120 h / 20 °C

15.2: 81 percent / PPTS / methanol / 1 h / 20 °C

16.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

16.2: BF₃*OEt / tetrahydrofuran / 1 h / -78 °C

With pyridine; 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; n-butyllithium; formic acid; N-methyl-2-indolinone; oxalyl dichloride; tributylphosphine; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ol052039k

upstream raw materials:

prop-1-yne

(4S,5R)-5,6-Dihydroxy-4-methyl-hexanoic acid methoxy-methyl-amide

(E)-(4S,5R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-4-methyl-hex-2-enoic acid methoxy-methyl-amide

Triethyl-[(1R,2S)-1-(4-methoxy-benzyloxymethyl)-2-methyl-but-3-ynyloxy]-silane