(3S,5R)-3,5-dimethyl-1-O-tert-butyldiphenylsilyl-7-O-triphenylmethyl-heptane-1,7-diol

Base Information

• Chemical Name: (3S,5R)-3,5-dimethyl-1-O-tert-butyldiphenylsilyl-7-O-triphenylmethyl-heptane-1,7-diol
• CAS No.: 103233-20-1
• Molecular Formula: C₄₄H₅₂O₂Si
• Molecular Weight: 640.981

Synonyms:(3S,5R)-3,5-dimethyl-1-O-tert-butyldiphenylsilyl-7-O-triphenylmethyl-heptane-1,7-diol

Chemical Property of (3S,5R)-3,5-dimethyl-1-O-tert-butyldiphenylsilyl-7-O-triphenylmethyl-heptane-1,7-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-3,5-dimethyl-1-O-tert-butyldiphenylsilyl-7-O-triphenylmethyl-heptane-1,7-diol

There total 24 articles about (3S,5R)-3,5-dimethyl-1-O-tert-butyldiphenylsilyl-7-O-triphenylmethyl-heptane-1,7-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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (3S,5R)-3,5-dimethyl-1-O-tert-butyldiphenylsilyl-7-O-triphenylmethyl-heptane-1,7-diol (103233-20-1)

Guidance literature:

Multi-step reaction with 18 steps

1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

3: 30percent H₂O₂ / 0 °C

4: 1.) CuBr*Me₂S / 1.) ether, hexane, 0 deg C, 6 min; 2.) -23 deg C, 20 min.

5: 96 percent / borane-dimethylsulphide complex / tetrahydrofuran / 15 h / Ambient temperature

6: pyridine / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / Ambient temperature

7: 92 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

8: pyridine / 48 h / Ambient temperature

9: sodium methoxide / methanol / 0.25 h / 0 °C

10: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, hexane, 0 deg C, 20 min; 2.) THF, hexane, 0 deg C to RT 3.) THF, 15 h

11: EDAC, DMAP / CH₂Cl₂ / 0.33 h / Ambient temperature

12: m-CPBA / CH₂Cl₂ / 0.17 h / -23 °C

13: CaCO₃, pyridine / toluene / 0.67 h / Heating

14: 1.) CuBr*Me₂S / 1.) ether, 0 deg C, 20 min; 2.) ether, -23 deg C, 20 min.

15: 94 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

16: 84 percent / pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

17: pyridine, DMAP / 1 h / Ambient temperature

18: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone (99315-76-1) → (3S,5R)-3,5-dimethyl-1-O-tert-butyldiphenylsilyl-7-O-triphenylmethyl-heptane-1,7-diol (103233-20-1)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) CuBr*Me₂S / 1.) ether, hexane, 0 deg C, 6 min; 2.) -23 deg C, 20 min.

2: 96 percent / borane-dimethylsulphide complex / tetrahydrofuran / 15 h / Ambient temperature

3: pyridine / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / Ambient temperature

4: 92 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

5: pyridine / 48 h / Ambient temperature

6: sodium methoxide / methanol / 0.25 h / 0 °C

7: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, hexane, 0 deg C, 20 min; 2.) THF, hexane, 0 deg C to RT 3.) THF, 15 h

8: EDAC, DMAP / CH₂Cl₂ / 0.33 h / Ambient temperature

9: m-CPBA / CH₂Cl₂ / 0.17 h / -23 °C

10: CaCO₃, pyridine / toluene / 0.67 h / Heating

11: 1.) CuBr*Me₂S / 1.) ether, 0 deg C, 20 min; 2.) ether, -23 deg C, 20 min.

12: 94 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

13: 84 percent / pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

14: pyridine, DMAP / 1 h / Ambient temperature

15: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; sodium methylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

(4S,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-methyldihydrofuran-2(3H)-one (103233-14-3) → (3S,5R)-3,5-dimethyl-1-O-tert-butyldiphenylsilyl-7-O-triphenylmethyl-heptane-1,7-diol (103233-20-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 96 percent / borane-dimethylsulphide complex / tetrahydrofuran / 15 h / Ambient temperature

2: pyridine / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / Ambient temperature

3: 92 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

4: pyridine / 48 h / Ambient temperature

5: sodium methoxide / methanol / 0.25 h / 0 °C

6: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, hexane, 0 deg C, 20 min; 2.) THF, hexane, 0 deg C to RT 3.) THF, 15 h

7: EDAC, DMAP / CH₂Cl₂ / 0.33 h / Ambient temperature

8: m-CPBA / CH₂Cl₂ / 0.17 h / -23 °C

9: CaCO₃, pyridine / toluene / 0.67 h / Heating

10: 1.) CuBr*Me₂S / 1.) ether, 0 deg C, 20 min; 2.) ether, -23 deg C, 20 min.

11: 94 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

12: 84 percent / pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

13: pyridine, DMAP / 1 h / Ambient temperature

14: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; sodium methylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)87683-3

upstream raw materials:

Methanesulfonic acid (1S,2S)-1-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-2-methyl-4-trityloxy-butyl ester

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

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

L-glutamic acid

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