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

Base Information

Chemical Name:ethyl (2R,3S)-2-benzyl-4-hydroxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanoate
CAS No.:1255239-79-2
Molecular Formula:C₂₇H₃₆O₁₃
Molecular Weight:568.575
Hs Code.:

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

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Chemical Property of ethyl (2R,3S)-2-benzyl-4-hydroxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanoate

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

There total 3 articles about ethyl (2R,3S)-2-benzyl-4-hydroxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanoate 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: 74.0%

: 1431382-26-1
ethyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsilyloxy)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanoate

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.3390/molecules18021933

Reference yield:

: 142775-59-5
ethyl (3S)-3-O-tert-butyldimethylsilyl-3,4-dihydroxybutanate

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

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium; lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -45 °C / Inert atmosphere

1.2: 0.5 h / -45 °C / Inert atmosphere

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

2.2: 0.5 h / -20 - 20 °C / Inert atmosphere; Molecular sieve

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.3390/molecules18021933

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.3390/molecules18021933