(3R,4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-hexane-1,4-diol

Base Information

• Chemical Name: (3R,4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-hexane-1,4-diol
• CAS No.: 105676-53-7
• Molecular Formula: C₁₂H₂₄O₄
• Molecular Weight: 232.32
• Mol file: 105676-53-7.mol

Synonyms:(3R,4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-hexane-1,4-diol

Chemical Property of (3R,4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-hexane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-hexane-1,4-diol

There total 1 articles about (3R,4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-hexane-1,4-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) → (3R,4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-hexane-1,4-diol (105676-53-7)

Guidance literature:

Multi-step reaction with 17 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: LiAlH₄ / diethyl ether / 1 h / 25 °C

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; 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; diethyl ether; dichloromethane; water; toluene;

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

Reference yield: 96.0%

(3R,4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-hexane-1,4-diol (105676-53-7) + tert-butylchlorodiphenylsilane (58479-61-1) → 3,5,6-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-7-O-tert-butyldiphenylsilyl-D-altro-heptitol (105676-54-8)

Guidance literature:

With pyridine; dmap; In dichloromethane;

Reference yield:

(3R,4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-hexane-1,4-diol (105676-53-7) → (3R,4S,5R,7S)-1,4,9-trihydroxy-3,5,7-trimethyl-9-O-tert-butyldiphenylsilyl-nonane (105676-34-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / DMAP, pyridine / CH₂Cl₂

2: Et₃N / CH₂Cl₂

3: LiAlH₄ / diethyl ether

4: aq. AcOH

5: pyridime

6: NaOMe / methanol

7: tetrahydrofuran / 0 - 25 °C

8: EDAC*HCl, DMPA / CH₂Cl₂

9: 1)H₂O₂, 2) CaCO₃ / 1) 0 deg C, CH₂Cl₂, 2) toluene, reflux

10: 88 percent / LiAlH₄ / diethyl ether

With pyridine; dmap; lithium aluminium tetrahydride; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; dihydrogen peroxide; sodium methylate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

upstream raw materials:

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

Downstream raw materials:

3,5,6-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-7-O-tert-butyldiphenylsilyl-D-altro-heptitol

1,2-anhydro-3,4,5,6-tetradeoxy-3,5-di-C-methyl-5-O-tert-butyldiphenyl-silyl-D-arabino-heptitol

3,4,5,6-tetradeoxy-3,5-di-C-methyl-7-O-tert-butyldiphenylsilyl-D-arabino-heptitol

(3R,4S,5R,7S)-1,4,9-trihydroxy-3,5,7-trimethyl-9-O-tert-butyldiphenylsilyl-nonane