ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate

Base Information

Chemical Name:ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate
CAS No.:729596-15-0
Molecular Formula:C₁₉H₂₆O₈
Molecular Weight:382.411
Hs Code.:

Synonyms:ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate

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Chemical Property of ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate

Chemical Property:

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Technology Process of ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate

There total 1 articles about ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate 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:

: 108788-49-4
ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

: 729596-15-0
ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate

: 729596-16-1
ethyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-L-ido-heptofuranuronate

Guidance literature:: With Hydroquinone 1,4-phthalazinediyl diether; potassium carbonate; potassium hexacyanoferrate(III); potassium osmate(VI); methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 24h;
DOI:10.1021/jo049509t

Reference yield:

: 729596-15-0
ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate

: [(1R,2R)-2-Hydroxy-1-hydroxymethyl-2-((2R,3R,4R)-3,4,5-trihydroxy-tetrahydro-furan-2-yl)-ethyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridine; thionyl chloride / CH₂Cl₂ / 0.33 h / 0 °C

1.2: 86 percent / NaIO₄ / RuCl₃*3H₂O / acetonitrile; H₂O / 0.17 h / 0 °C

2.1: NaN₃ / acetone; H₂O / 2 h / 0 - 25 °C

2.2: 81.7 percent / H₂SO₄ / diethyl ether; H₂O / 6 h / 25 °C

3.1: LiAlH₄ / tetrahydrofuran / 3 h / 0 - 25 °C

4.1: ammonium formate / Pd/C / methanol / 1 h / Heating

5.1: 0.47 g / NaHCO₃ / methanol; H₂O / 3.5 h / 0 - 25 °C

6.1: TFA / H₂O / 2.5 h / 25 °C

With pyridine; lithium aluminium tetrahydride; thionyl chloride; sodium azide; ammonium formate; sodium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1021/jo049509t

Reference yield:

: 729596-15-0
ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate

: 729596-19-4
6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine; thionyl chloride / CH₂Cl₂ / 0.33 h / 0 °C

1.2: 86 percent / NaIO₄ / RuCl₃*3H₂O / acetonitrile; H₂O / 0.17 h / 0 °C

2.1: NaN₃ / acetone; H₂O / 2 h / 0 - 25 °C

2.2: 81.7 percent / H₂SO₄ / diethyl ether; H₂O / 6 h / 25 °C

3.1: LiAlH₄ / tetrahydrofuran / 3 h / 0 - 25 °C

4.1: ammonium formate / Pd/C / methanol / 1 h / Heating

5.1: 0.47 g / NaHCO₃ / methanol; H₂O / 3.5 h / 0 - 25 °C

With pyridine; lithium aluminium tetrahydride; thionyl chloride; sodium azide; ammonium formate; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1021/jo049509t