(2R,3S)-2-benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanolide

Base Information

Chemical Name:(2R,3S)-2-benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanolide
CAS No.:1255239-78-1
Molecular Formula:C₂₅H₃₀O₁₂
Molecular Weight:522.506
Hs Code.:

Synonyms:(2R,3S)-2-benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanolide

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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 (2R,3S)-2-benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanolide

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Technology Process of (2R,3S)-2-benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanolide

There total 6 articles about (2R,3S)-2-benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanolide 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: 95.0%

: 1431382-42-1
(2R,3S)-2-benzyl-3-(β-D-glucopyranosyloxy)butanolide

: 108-24-7
acetic anhydride

: 1255239-78-1
(2R,3S)-2-benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanolide

Guidance literature:: With pyridine; at 20 ℃;
DOI:10.3390/molecules18021933

Reference yield: 64.0%

: 1255239-79-2
ethyl (2R,3S)-2-benzyl-4-hydroxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanoate

: 1255239-78-1
(2R,3S)-2-benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanolide

Guidance literature:: With toluene-4-sulfonic acid; In 1,4-dioxane; at 20 ℃;
DOI:10.3390/molecules18021933

Reference yield:

: 1431382-21-6
ethyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsilyloxy)-3-hydroxybutanoate

: 1255239-78-1
(2R,3S)-2-benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanolide

Guidance literature:: Multi-step reaction with 3 steps

1.1: dichloromethane / 1 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 0.5 h / -20 - 20 °C / Inert atmosphere; Molecular sieve

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

3.1: toluene-4-sulfonic acid / 1,4-dioxane / 20 °C

With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.3390/molecules18021933