3,5-dideoxy-3,5-di-C-methyl-5,6-O-isopropylidene-D-talitol

Base Information

Chemical Name:3,5-dideoxy-3,5-di-C-methyl-5,6-O-isopropylidene-D-talitol
CAS No.:105676-40-2
Molecular Formula:C₁₁H₂₂O₄
Molecular Weight:218.293
Hs Code.:

Synonyms:3,5-dideoxy-3,5-di-C-methyl-5,6-O-isopropylidene-D-talitol

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Chemical Property of 3,5-dideoxy-3,5-di-C-methyl-5,6-O-isopropylidene-D-talitol

Chemical Property:

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Technology Process of 3,5-dideoxy-3,5-di-C-methyl-5,6-O-isopropylidene-D-talitol

There total 1 articles about 3,5-dideoxy-3,5-di-C-methyl-5,6-O-isopropylidene-D-talitol 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

: 105676-40-2
3,5-dideoxy-3,5-di-C-methyl-5,6-O-isopropylidene-D-talitol

Guidance literature:: Multi-step reaction with 19 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

8: dimethoxypropane, conc. HCl / 1.5 h / Ambient temperature

9: 95 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

10: 92 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

11: sodium methoxide / methanol / 0.5 h / 0 °C

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

13: EDAC, DMAP / CH₂Cl₂ / 0.33 h

14: m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

15: pyridine, CaCO₃ / toluene / 1 h / Heating

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

17: 1.) hexamethyldisilazan, n-butyl lithium, 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 20 min; 2.) THF, -78 deg C, 30 min; 3.) THF, -78 to 50 deg C, 40 min.

18: 73 percent / NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

19: 1.) sodium metaperiodate 2.) NaBH₄ / 1.) H₂O, RT, 10 min; 2.) H₂O, RT, 10 min.

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; sodium periodate; n-butyllithium; copper(I) bromide dimethylsulfide complex; MoO₅*pyridine*HMPA; dimethoxypropane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; nickel; 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; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield: 100.0%

: 105676-40-2
3,5-dideoxy-3,5-di-C-methyl-5,6-O-isopropylidene-D-talitol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 105676-41-3
(2R,3R,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-pentan-3-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1016/j.tet.2007.02.011

Reference yield:

: 105676-40-2
3,5-dideoxy-3,5-di-C-methyl-5,6-O-isopropylidene-D-talitol

: Acetic acid (1R,2S,3R)-3-acetoxy-5-(4-bromo-phenylcarbamoyloxy)-1-[(R)-3-((3S,4R,5S,6S)-4,6-dimethyl-2,8-dioxa-bicyclo[3.2.1]oct-3-yl)-1-methyl-propyl]-2-methyl-pentyl ester

Guidance literature:: Multi-step reaction with 20 steps

1: imidazole / dimethylformamide / 0 °C

2: NaH / dimethylformamide; tetrahydrofuran / 23 °C

3: AcOH, H₂O / ethanol / 23 °C

4: pyridine / 0 °C

5: K₂CO₃ / methanol / 0 °C

6: n-BuLi / tetrahydrofuran / 23 °C

7: NaH / dimethylformamide; tetrahydrofuran / 23 °C

8: CuCl₂, CuO / acetone; H₂O / Heating

9: NaBH₄ / ethanol / -30 °C

10: i-Pr₂NEt / CH₂Cl₂ / 23 °C

11: n-Bu₄NF / tetrahydrofuran / 23 °C

12: I₂, PPh₃, imidazole / benzene / 10 °C

13: acetonitrile / 90 °C

14: NaN(TMS)2 / toluene / -78 - -23 °C

15: H₂ / Pd/C / ethanol / 23 °C

16: HCl / methanol; H₂O / 23 °C

17: pyridine / 80 °C

18: 23 °C

19: AcOH, H₂O / 80 °C

20: pyridine / 23 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; water; hydrogen; iodine; sodium hexamethyldisilazane; sodium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(II) oxide; copper dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)61370-9