(2R,4R,6R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptan-4-ol

Base Information

• Chemical Name: (2R,4R,6R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptan-4-ol
• CAS No.: 101382-91-6
• Molecular Formula: C₃₀H₄₆O₄Si
• Molecular Weight: 498.778
• Mol file: 101382-91-6.mol

Synonyms:(2R,4R,6R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptan-4-ol

Chemical Property of (2R,4R,6R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptan-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,6R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptan-4-ol

There total 10 articles about (2R,4R,6R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptan-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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (2R,4R,6R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptan-4-ol (101382-91-6)

Guidance literature:

Multi-step reaction with 10 steps

2: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 10 min

3: BH₃*Me₂S / tetrahydrofuran / 1 h

4: imidazole / dimethylformamide

5: NaOMe / methanol / 0.25 h / 0 °C

6: 1.) LiN(TMS)2, 2.) ethyl(dimethylaminoethyl) carbodiimide HCl, DMAP / 1.) THF, 0 deg C, then 25 deg C, 2.) Et₂O

7: 1.) NaIO₄, 2.) pyr. / 1.) H₂O, 2.) toluene, reflux, 3 h

8: H₂ / Pd/C / ethyl acetate

9: LAH / tetrahydrofuran / 2 h / -10 °C

10: PPTS / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide borane complex; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)80903-5

Reference yield:

Naphthalene-2-sulfonic acid (2S,4R)-5-(tert-butyl-diphenyl-silanyloxy)-4-methyl-tetrahydro-furan-2-ylmethyl ester → (2R,4R,6R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptan-4-ol (101382-91-6)

Guidance literature:

Multi-step reaction with 6 steps

1: NaOMe / methanol / 0.25 h / 0 °C

2: 1.) LiN(TMS)2, 2.) ethyl(dimethylaminoethyl) carbodiimide HCl, DMAP / 1.) THF, 0 deg C, then 25 deg C, 2.) Et₂O

3: 1.) NaIO₄, 2.) pyr. / 1.) H₂O, 2.) toluene, reflux, 3 h

4: H₂ / Pd/C / ethyl acetate

5: LAH / tetrahydrofuran / 2 h / -10 °C

6: PPTS / CH₂Cl₂

With pyridine; dmap; sodium periodate; lithium aluminium tetrahydride; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(01)80903-5

Reference yield:

Naphthalene-2-sulfonic acid (2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-ylmethyl ester → (2R,4R,6R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptan-4-ol (101382-91-6)

Guidance literature:

Multi-step reaction with 8 steps

1: BH₃*Me₂S / tetrahydrofuran / 1 h

2: imidazole / dimethylformamide

3: NaOMe / methanol / 0.25 h / 0 °C

4: 1.) LiN(TMS)2, 2.) ethyl(dimethylaminoethyl) carbodiimide HCl, DMAP / 1.) THF, 0 deg C, then 25 deg C, 2.) Et₂O

5: 1.) NaIO₄, 2.) pyr. / 1.) H₂O, 2.) toluene, reflux, 3 h

6: H₂ / Pd/C / ethyl acetate

7: LAH / tetrahydrofuran / 2 h / -10 °C

8: PPTS / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide borane complex; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)80903-5

upstream raw materials:

3,4-dihydro-2H-pyran

(2R,4R,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-heptane-1,4-diol

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

L-glutamic acid

Downstream raw materials:

(2R,6R)-7-(t-butyldiphenylsilyloxy)-2,6-dimethylheptan-1-ol

Methanesulfonic acid (R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-1-[(R)-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-butyl ester

Refernces