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

Base Information

• Chemical Name: (2R,6R)-7-(t-butyldiphenylsilyloxy)-2,6-dimethylheptan-1-ol
• CAS No.: 101382-93-8
• Molecular Formula: C₂₅H₃₈O₂Si
• Molecular Weight: 398.661
• Mol file: 101382-93-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about (2R,6R)-7-(t-butyldiphenylsilyloxy)-2,6-dimethylheptan-1-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,6R)-7-(t-butyldiphenylsilyloxy)-2,6-dimethylheptan-1-ol (101382-93-8)

Guidance literature:

Multi-step reaction with 12 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

12: 1.) LAH, 2.) 0.5 M HCl / 1.) THF, -10 deg C, 2 h, 2.) H₂O, MeOH, 2 h

With pyridine; 1H-imidazole; hydrogenchloride; 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:

tert-butylchlorodiphenylsilane (58479-61-1) → (2R,6R)-7-(t-butyldiphenylsilyloxy)-2,6-dimethylheptan-1-ol (101382-93-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

2: 99 percent / dimethylsulfoxide / 2 h / 120 °C

3: 1.) diisobutylaluminum hydride, 2.) aq. HCl, aq. potassium tartrate / 1.) toluene, 0 deg C, 30 min, 2.) toluene, 0 deg C, 15 min

4: 1.) triphenylmethane, LDA / 1.) THF, a) -78 deg C, 30 min, b) RT, 30 min, 2.) THF, a) -78 deg C, 30 min, b) 0 deg C, 1 h

5: H₂, sodium nitrite / 10percent Pd/C / methanol / 12 h

With 1H-imidazole; hydrogenchloride; triphenylmethane; hydrogen; diisobutylaluminium hydride; potassium tartrate; lithium diisopropyl amide; sodium nitrite; palladium on activated charcoal; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(96)00916-7

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (2R,6R)-7-(t-butyldiphenylsilyloxy)-2,6-dimethylheptan-1-ol (101382-93-8)

Guidance literature:

Multi-step reaction with 13 steps

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

4: BH₃*Me₂S / tetrahydrofuran / 1 h

5: imidazole / dimethylformamide

6: NaOMe / methanol / 0.25 h / 0 °C

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

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

9: H₂ / Pd/C / ethyl acetate

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

11: PPTS / CH₂Cl₂

13: 1.) LAH, 2.) 0.5 M HCl / 1.) THF, -10 deg C, 2 h, 2.) H₂O, MeOH, 2 h

With pyridine; 1H-imidazole; hydrogenchloride; 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:

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

(E)-(2R,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-2,6-dimethyl-hept-3-en-1-ol

(2S)-1-bromo-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropane

tert-butylchlorodiphenylsilane

Downstream raw materials:

[(2R,6R)-8-Benzenesulfonyl-2,6-dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octyloxy]-tert-butyl-diphenyl-silane

tert-Butyl-[(2R,6R)-2,6-dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octyloxy]-diphenyl-silane

((2R,6R)-7-Bromo-2,6-dimethyl-heptyloxy)-tert-butyl-diphenyl-silane

(E)-(5R,9R)-5,9-Dimethyl-11-(2,6,6-trimethyl-cyclohex-1-enyl)-undec-2-enoic acid ethyl ester

Refernces

• 1、 Hanessian, Stephen,Murray, Peter J.,Sahoo, Soumya P.. "A Tactically Novel Alternative to Acyclic Stereoselection Based on the Concept of a Replicating Chiron - 1,5-C-Methyl Substitution". . p. 5623 - 5626. Retrieved 2007/10/02.