5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester

Base Information

Chemical Name:5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester
CAS No.:91738-42-0
Molecular Formula:C₂₅H₃₂O₁₆
Molecular Weight:588.519
Hs Code.:

5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester

Synonyms:5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester

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Chemical Property of 5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester

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Technology Process of 5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester

There total 11 articles about 5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester 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:

: 91738-41-9
5-<<2-O-(2,3,5-O-Acetyl-β-D-apiofuranosyl)-3-O-benzyl-4,6-O-benzyliden-β-D-glucopyranosyl>oxy>-2-hydroxybenzoesaeure-methylester

: 91738-42-0
5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol; Yield given; Ambient temperature;

Reference yield:

: 34339-69-0
2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide

: 91738-42-0
5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 47 percent / drierite, Ag₂O, quinoline / 3 h

2: 66 percent / 0.1 N NaOCH₃ / methanol / 0.33 h / Heating

3: 83 percent / ZnCl₂ (anhydrous) / 2 h / Ambient temperature

4: 1.) SnCl₄ / 1.) CH₂Cl₂, RT, 10 min; 2.) CH₂Cl₂, 4-6 deg C, 2 h

5: H₂ / Pd/C / ethanol / Ambient temperature

With quinoline; calcium sulfate; hydrogen; sodium methylate; tin(IV) chloride; zinc(II) chloride; silver(l) oxide; palladium on activated charcoal; In methanol; ethanol;

Reference yield:

: 35354-34-8
5-O-Acetylgentisinsaeure-methylester

: 91738-42-0
5-[(2S,3R,4S,5S,6R)-3-((2S,3R,4S)-3,4-Diacetoxy-4-acetoxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-hydroxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / K₂CO₃ (anhydrous) / acetone / 12 h / Heating

2: 80 percent / 0.1 N NaOCH₃ / methanol / 12 h / Heating

3: 47 percent / drierite, Ag₂O, quinoline / 3 h

4: 66 percent / 0.1 N NaOCH₃ / methanol / 0.33 h / Heating

5: 83 percent / ZnCl₂ (anhydrous) / 2 h / Ambient temperature

6: 1.) SnCl₄ / 1.) CH₂Cl₂, RT, 10 min; 2.) CH₂Cl₂, 4-6 deg C, 2 h

7: H₂ / Pd/C / ethanol / Ambient temperature

With quinoline; calcium sulfate; hydrogen; sodium methylate; tin(IV) chloride; potassium carbonate; zinc(II) chloride; silver(l) oxide; palladium on activated charcoal; In methanol; ethanol; acetone;