methyl 1,2-di-O-acetyl-4-O-allyl-3-O-benzyl-β-L-idopyranosiduronate

Base Information

Chemical Name:methyl 1,2-di-O-acetyl-4-O-allyl-3-O-benzyl-β-L-idopyranosiduronate
CAS No.:615543-24-3
Molecular Formula:C₂₁H₂₆O₉
Molecular Weight:422.432
Hs Code.:

Synonyms:methyl 1,2-di-O-acetyl-4-O-allyl-3-O-benzyl-β-L-idopyranosiduronate

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Chemical Property of methyl 1,2-di-O-acetyl-4-O-allyl-3-O-benzyl-β-L-idopyranosiduronate

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Technology Process of methyl 1,2-di-O-acetyl-4-O-allyl-3-O-benzyl-β-L-idopyranosiduronate

There total 11 articles about methyl 1,2-di-O-acetyl-4-O-allyl-3-O-benzyl-β-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:

: 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

: 615543-24-3
methyl 1,2-di-O-acetyl-4-O-allyl-3-O-benzyl-β-L-idopyranosiduronate

Guidance literature:: Multi-step reaction with 8 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: 70 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 72 h

7.1: trifluoroacetic acid / H₂O / 0.5 h

8.1: pyridine; DMAP / CH₂Cl₂

With pyridine; dmap; sodium periodate; n-butyllithium; 4 A molecular sieve; silica gel; (+)-10-camphorsulfonic acid; trifluoroacetic acid; copper(II) oxide; copper dichloride; silver(l) oxide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0340760

Reference yield:

: 100-39-0
benzyl bromide

: 615543-24-3
methyl 1,2-di-O-acetyl-4-O-allyl-3-O-benzyl-β-L-idopyranosiduronate

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH; tetrabutylammonium iodide / tetrahydrofuran / 14 h / 20 °C

2.1: 17.8 g / acetic acid / H₂O / 16 h / 20 °C

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

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

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

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

5.2: 437 mg / K₂CO₃ / CH₂Cl₂; methanol / 1.5 h / 20 °C

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

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

7.2: 199 mg / Dowex 50W acidic resin / methanol / 0.33 h / 20 °C

8.1: 70 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 72 h

9.1: trifluoroacetic acid / H₂O / 0.5 h

10.1: pyridine; DMAP / CH₂Cl₂

With pyridine; dmap; sodium periodate; n-butyllithium; 4 A molecular sieve; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; (+)-10-camphorsulfonic acid; trifluoroacetic acid; copper(II) oxide; copper dichloride; silver(l) oxide; 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

: 615543-24-3
methyl 1,2-di-O-acetyl-4-O-allyl-3-O-benzyl-β-L-idopyranosiduronate

Guidance literature:: Multi-step reaction with 9 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: 70 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 72 h

8.1: trifluoroacetic acid / H₂O / 0.5 h

9.1: pyridine; DMAP / CH₂Cl₂

With pyridine; dmap; sodium periodate; n-butyllithium; 4 A molecular sieve; silica gel; acetic acid; (+)-10-camphorsulfonic acid; trifluoroacetic acid; copper(II) oxide; copper dichloride; silver(l) oxide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0340760