methyl 3-O-benzyl-1,2-O-isopropylidene-4-O-levulinoyl-α-L-idopyranosiduronate

Base Information

Chemical Name:methyl 3-O-benzyl-1,2-O-isopropylidene-4-O-levulinoyl-α-L-idopyranosiduronate
CAS No.:615543-00-5
Molecular Formula:C₂₂H₂₈O₉
Molecular Weight:436.459
Hs Code.:

Synonyms:methyl 3-O-benzyl-1,2-O-isopropylidene-4-O-levulinoyl-α-L-idopyranosiduronate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl 3-O-benzyl-1,2-O-isopropylidene-4-O-levulinoyl-α-L-idopyranosiduronate

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Technology Process of methyl 3-O-benzyl-1,2-O-isopropylidene-4-O-levulinoyl-α-L-idopyranosiduronate

There total 11 articles about methyl 3-O-benzyl-1,2-O-isopropylidene-4-O-levulinoyl-α-L-idopyranosiduronate 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: 98.0%

: 123-76-2
levulinic acid

: 444118-44-9
1,2-O-isopropylidene-3-O-benzyl-4-O-trichloroacetyl-6-methyl-α-L-idonic acid

: 615543-00-5
methyl 3-O-benzyl-1,2-O-isopropylidene-4-O-levulinoyl-α-L-idopyranosiduronate

Guidance literature:: With dmap; bis-2-propyl carbonate; In dichloromethane; at 20 ℃; for 11h;
DOI:10.1021/jo0340760

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 615543-00-5
methyl 3-O-benzyl-1,2-O-isopropylidene-4-O-levulinoyl-α-L-idopyranosiduronate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium periodate; silica gel / CH₂Cl₂; H₂O / 1.5 h

2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

2.2: tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C

3.1: CuCl₂; CuO / H₂O; CH₂Cl₂ / 0.08 h / 20 °C

3.2: 437 mg / K₂CO₃ / CH₂Cl₂; methanol / 1.5 h / 20 °C

4.1: trifluoroacetic acid / H₂O / 0.58 h / 20 °C

5.1: (+)-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

5.2: 199 mg / Dowex 50W acidic resin / methanol / 0.33 h / 20 °C

6.1: 98 percent / DIPC; DMAP / CH₂Cl₂ / 11 h / 20 °C

With dmap; sodium periodate; n-butyllithium; bis-2-propyl carbonate; silica gel; (+)-10-camphorsulfonic acid; trifluoroacetic acid; copper(II) oxide; copper dichloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0340760

Reference yield:

: 18685-18-2
3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

: 615543-00-5
methyl 3-O-benzyl-1,2-O-isopropylidene-4-O-levulinoyl-α-L-idopyranosiduronate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 17.8 g / acetic acid / H₂O / 16 h / 20 °C

2.1: sodium periodate; silica gel / CH₂Cl₂; H₂O / 1.5 h

3.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

3.2: tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C

4.1: CuCl₂; CuO / H₂O; CH₂Cl₂ / 0.08 h / 20 °C

4.2: 437 mg / K₂CO₃ / CH₂Cl₂; methanol / 1.5 h / 20 °C

5.1: trifluoroacetic acid / H₂O / 0.58 h / 20 °C

6.1: (+)-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

6.2: 199 mg / Dowex 50W acidic resin / methanol / 0.33 h / 20 °C

7.1: 98 percent / DIPC; DMAP / CH₂Cl₂ / 11 h / 20 °C

With dmap; sodium periodate; n-butyllithium; bis-2-propyl carbonate; silica gel; acetic acid; (+)-10-camphorsulfonic acid; trifluoroacetic acid; copper(II) oxide; copper dichloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0340760