(2S,3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2,4-triol

Base Information

Chemical Name:(2S,3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2,4-triol
CAS No.:115495-40-4
Molecular Formula:C₂₂H₃₂O₄Si
Molecular Weight:388.579
Hs Code.:

Synonyms:(2S,3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2,4-triol

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Chemical Property of (2S,3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2,4-triol

Chemical Property:

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Technology Process of (2S,3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2,4-triol

There total 13 articles about (2S,3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2,4-triol 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:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 115495-40-4
(2S,3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2,4-triol

Guidance literature:: Multi-step reaction with 7 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.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

5: 1.) n-butyl lithium, hexamethyldisilazane 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 10 min; 2.) THF, -78 deg C, 20 min; 3.) THF, -60 deg C, 45 min.

6: 62 percent / Raney-nickel / methanol / 18 h / Ambient temperature

7: NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

With dmap; sodium tetrahydroborate; n-butyllithium; MoO₅*pyridine*HMPA; dihydrogen peroxide; nickel; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

: 99315-76-1
(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone

: 115495-40-4
(2S,3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2,4-triol

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / tetrahydrofuran / -78 °C

2: 85 percent / oxodiperoxymolybdenum(pyridine)hexamethylphosphoramide / tetrahydrofuran / -78 °C

3: 65 percent / Raney nickel / tetrahydrofuran

4: NaBH₄ / tetrahydrofuran; H₂O

With sodium tetrahydroborate; MoO₅*pyridine*HMPA; nickel; In tetrahydrofuran; water;

Reference yield:

: 92512-33-9
(3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one

: 115495-40-4
(2S,3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2,4-triol

Guidance literature:: Multi-step reaction with 9 steps

1: tetrahydrofuran / 0.25 h / Ambient temperature

2: Raney nickel / tetrahydrofuran / 4 h / Heating

3: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

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

5: 30percent H₂O₂ / 0 °C

6: 1.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

7: 1.) n-butyl lithium, hexamethyldisilazane 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 10 min; 2.) THF, -78 deg C, 20 min; 3.) THF, -60 deg C, 45 min.

8: 62 percent / Raney-nickel / methanol / 18 h / Ambient temperature

9: NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

With dmap; sodium tetrahydroborate; n-butyllithium; MoO₅*pyridine*HMPA; dihydrogen peroxide; nickel; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/S0040-4020(01)87683-3