5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol

Base Information

Chemical Name:5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol
CAS No.:124928-82-1
Molecular Formula:C₁₈H₂₅IO₃
Molecular Weight:416.299
Hs Code.:

Synonyms:5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol

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Chemical Property of 5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol

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Technology Process of 5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol

There total 19 articles about 5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol 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:

: 124928-81-0
[1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-eth-(E)-ylidene]-hydrazine

: 124928-82-1
5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol

Guidance literature:: With 1,1,3,3-tetramethylguanidine; iodine; In toluene; at 0 ℃; for 0.5h; Yield given;
DOI:10.1016/S0040-4039(00)84382-8

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 124928-82-1
5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol

Guidance literature:: Multi-step reaction with 14 steps

1: 73 percent / Mg / diethyl ether / 3.5 h / 23 °C

2: 1.) NaIO₄, 2.) LiAlH₄ / 1.) 24 deg C, 1 h, aqueous acetone, 2.) THF, 20 deg C, 20 min

3: 97 percent / imidazole / dimethylformamide / 2.66 h / 24 °C

4: pyridinium chlorochromate, molecular sieves 3 Angstroem / CH₂Cl₂ / 2 h / 22 °C

5: 85 percent / magnesium powder / tetrahydrofuran / 3 h / Ambient temperature

6: 1.) O₃, 2.) dimethyl sulfide / 1.) methylene dichloride, -78 deg C, 2.) room temperature

7: 88 percent / magnesium powder / diethyl ether / 1.5 h / 0 °C

8: 55 percent / NaH / tetrahydrofuran / 4 h / 21 °C

9: 95 percent / FeCl₃ / acetone / 1 h / 29 °C

10: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

11: NaIO₄ / acetone; H₂O / 3 h

12: 90.6 percent / magnesium powder / diethyl ether / 2 h / 27 °C

13: 98 percent / PCC, molecular sieves 3A / CH₂Cl₂ / 1.5 h / 25 °C

14: 1.) NH₂NH₂xH₂O, Et₃N, 2.) I₂, 1,1,3,3-tetramethylquanidine / 1.) ethanol, 70 deg C, 1 h, 2.) toluene, 0 deg C, 0.5 h

With 1H-imidazole; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide; 3 A molecular sieve; tetrabutyl ammonium fluoride; iodine; iron(III) chloride; sodium hydride; ozone; hydrazine hydrate; magnesium; triethylamine; pyridinium chlorochromate; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1246/bcsj.62.2618

Reference yield:

: 4159-66-4,105617-51-4,107494-47-3,138127-63-6,138127-64-7
(R)-1-((4R,5S)-5-((S)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol

: 124928-82-1
5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) NaIO₄, 2.) LiAlH₄ / 1.) 24 deg C, 1 h, aqueous acetone, 2.) THF, 20 deg C, 20 min

2: 97 percent / imidazole / dimethylformamide / 2.66 h / 24 °C

3: pyridinium chlorochromate, molecular sieves 3 Angstroem / CH₂Cl₂ / 2 h / 22 °C

4: 85 percent / magnesium powder / tetrahydrofuran / 3 h / Ambient temperature

5: 1.) O₃, 2.) dimethyl sulfide / 1.) methylene dichloride, -78 deg C, 2.) room temperature

6: 88 percent / magnesium powder / diethyl ether / 1.5 h / 0 °C

7: 55 percent / NaH / tetrahydrofuran / 4 h / 21 °C

8: 95 percent / FeCl₃ / acetone / 1 h / 29 °C

9: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

10: NaIO₄ / acetone; H₂O / 3 h

11: 90.6 percent / magnesium powder / diethyl ether / 2 h / 27 °C

12: 98 percent / PCC, molecular sieves 3A / CH₂Cl₂ / 1.5 h / 25 °C

13: 1.) NH₂NH₂xH₂O, Et₃N, 2.) I₂, 1,1,3,3-tetramethylquanidine / 1.) ethanol, 70 deg C, 1 h, 2.) toluene, 0 deg C, 0.5 h

With 1H-imidazole; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide; 3 A molecular sieve; tetrabutyl ammonium fluoride; iodine; iron(III) chloride; sodium hydride; ozone; hydrazine hydrate; magnesium; triethylamine; pyridinium chlorochromate; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1246/bcsj.62.2618