2,2-Dimethyl-propionic acid (2S,4R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,6-dimethyl-heptyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2S,4R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,6-dimethyl-heptyl ester
• CAS No.: 101382-87-0
• Molecular Formula: C₃₁H₄₈O₆SSi
• Molecular Weight: 576.87
• Mol file: 101382-87-0.mol

Synonyms:2,2-Dimethyl-propionic acid (2S,4R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,6-dimethyl-heptyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2S,4R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,6-dimethyl-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2S,4R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,6-dimethyl-heptyl ester

There total 14 articles about 2,2-Dimethyl-propionic acid (2S,4R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,6-dimethyl-heptyl ester 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) → 2,2-Dimethyl-propionic acid (2S,4R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,6-dimethyl-heptyl ester (101382-87-0)

Guidance literature:

Multi-step reaction with 11 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: 92 percent / MeOH / Raney Ni / 0.5 h

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

9: 70 percent / LAH / tetrahydrofuran / 2 h / -10 °C

10: 85 percent / pyr. / CH₂Cl₂

11: 1.) pyr., 2.) LAH / 1.) CH₂Cl₂, 2.) 0 deg C, 2 h

With pyridine; 1H-imidazole; methanol; dmap; lithium aluminium tetrahydride; dimethylsulfide borane complex; Li(TMS)2; sodium methylate; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; nickel; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → 2,2-Dimethyl-propionic acid (2S,4R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,6-dimethyl-heptyl ester (101382-87-0)

Guidance literature:

Multi-step reaction with 12 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: 92 percent / MeOH / Raney Ni / 0.5 h

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

10: 70 percent / LAH / tetrahydrofuran / 2 h / -10 °C

11: 85 percent / pyr. / CH₂Cl₂

12: 1.) pyr., 2.) LAH / 1.) CH₂Cl₂, 2.) 0 deg C, 2 h

With pyridine; 1H-imidazole; methanol; dmap; lithium aluminium tetrahydride; dimethylsulfide borane complex; Li(TMS)2; sodium methylate; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; nickel; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

tert-Butyl-((R)-2-methyl-3-oxiranyl-propoxy)-diphenyl-silane (101382-81-4) → 2,2-Dimethyl-propionic acid (2S,4R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,6-dimethyl-heptyl ester (101382-87-0)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 92 percent / MeOH / Raney Ni / 0.5 h

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

4: 70 percent / LAH / tetrahydrofuran / 2 h / -10 °C

5: 85 percent / pyr. / CH₂Cl₂

6: 1.) pyr., 2.) LAH / 1.) CH₂Cl₂, 2.) 0 deg C, 2 h

With pyridine; methanol; dmap; lithium aluminium tetrahydride; Li(TMS)2; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; nickel; In tetrahydrofuran; dichloromethane;

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

upstream raw materials:

2,2-Dimethyl-propionic acid (2S,4R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2,6-dimethyl-heptyl ester

methanesulfonyl chloride

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

L-glutamic acid

Downstream raw materials:

(2S,6R)-7-tert-butyldiphenylsilyloxy-2,6-dimethyl-1-heptanol

tert-Butyl-[(R)-2-methyl-3-((S)-4-methyl-tetrahydro-furan-2-yl)-propoxy]-diphenyl-silane

Refernces