ethyl (2R,3S)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanoate

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Chemical Name:ethyl (2R,3S)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanoate
CAS No.:1431382-27-2
Molecular Formula:C₃₄H₅₂O₁₄Si
Molecular Weight:712.864
Hs Code.:

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

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

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

There total 2 articles about ethyl (2R,3S)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)-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: 67.0%

: 1431382-22-7
ethyl (2R,3S)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-2-(4-methoxybenzyl)butanoate

: 74808-10-9
O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

: 1431382-27-2
ethyl (2R,3S)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanoate

Guidance literature:: ethyl (2R,3S)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-2-(4-methoxybenzyl)butanoate; O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate; In dichloromethane; at 20 ℃; for 1h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 - 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;
DOI:10.3390/molecules18021933

Reference yield:

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

: 1431382-27-2
ethyl (2R,3S)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanoate

Guidance literature:: Multi-step reaction with 2 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

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