1,2-anhydro-3-deoxy-3-C-methyl-4,5-O-isopropylidene-D-arabinitol

Base Information

Chemical Name:1,2-anhydro-3-deoxy-3-C-methyl-4,5-O-isopropylidene-D-arabinitol
CAS No.:105676-49-1
Molecular Formula:C₉H₁₆O₃
Molecular Weight:172.224
Hs Code.:

Synonyms:1,2-anhydro-3-deoxy-3-C-methyl-4,5-O-isopropylidene-D-arabinitol

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Chemical Property of 1,2-anhydro-3-deoxy-3-C-methyl-4,5-O-isopropylidene-D-arabinitol

Chemical Property:

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Technology Process of 1,2-anhydro-3-deoxy-3-C-methyl-4,5-O-isopropylidene-D-arabinitol

There total 1 articles about 1,2-anhydro-3-deoxy-3-C-methyl-4,5-O-isopropylidene-D-arabinitol 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

: 105676-49-1
1,2-anhydro-3-deoxy-3-C-methyl-4,5-O-isopropylidene-D-arabinitol

Guidance literature:: Multi-step reaction with 11 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

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; MoO₅*pyridine*HMPA; dimethoxypropane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; 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:

: 105676-49-1
1,2-anhydro-3-deoxy-3-C-methyl-4,5-O-isopropylidene-D-arabinitol

: 105676-33-3
(4R,5S)-5-[(1R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-pentyl]-4-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 15 steps

1: tetrahydrofuran / 0 - 25 °C

2: EDAC*HCl, DMAP / CH₂Cl₂

3: 1) m-CPBA, 2) CaCO₃ / 1) CH₂Cl₂, - 23 deg C, 2) toluene, reflux

4: 91 percent / diethyl ether / -23 °C

5: 90 percent / LiAlH₄ / diethyl ether

6: 96 percent / DMAP, pyridine / CH₂Cl₂

7: Et₃N / CH₂Cl₂

8: LiAlH₄ / diethyl ether

9: aq. AcOH

10: pyridime

11: NaOMe / methanol

12: tetrahydrofuran / 0 - 25 °C

13: EDAC*HCl, DMPA / CH₂Cl₂

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

15: 90 percent / Me₂CuLi / diethyl ether / -23 °C

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

Reference yield:

: 105676-49-1
1,2-anhydro-3-deoxy-3-C-methyl-4,5-O-isopropylidene-D-arabinitol

: 105676-37-7
(3R,5S,7S)-1,9-dihydroxy-3,5,7-trimethyl-9-O-tert-butyldiphenylsilyl-1-O-triphenylmethyl-nonane

Guidance literature:: Multi-step reaction with 18 steps

1: tetrahydrofuran / 0 - 25 °C

2: EDAC*HCl, DMAP / CH₂Cl₂

3: 1) m-CPBA, 2) CaCO₃ / 1) CH₂Cl₂, - 23 deg C, 2) toluene, reflux

4: 91 percent / diethyl ether / -23 °C

5: 90 percent / LiAlH₄ / diethyl ether

6: 96 percent / DMAP, pyridine / CH₂Cl₂

7: Et₃N / CH₂Cl₂

8: LiAlH₄ / diethyl ether

9: aq. AcOH

10: pyridime

11: NaOMe / methanol

12: tetrahydrofuran / 0 - 25 °C

13: EDAC*HCl, DMPA / CH₂Cl₂

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

15: 88 percent / LiAlH₄ / diethyl ether

16: acetonitrile

17: Et₃N / CH₂Cl₂

18: 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; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;