(2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Base Information

Chemical Name:(2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
CAS No.:1326704-13-5
Molecular Formula:C₂₈H₃₆O₁₂
Molecular Weight:564.587
Hs Code.:

Synonyms:(2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

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Chemical Property of (2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

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Technology Process of (2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

There total 5 articles about (2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 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: 65.0%

: 74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,127061-80-7,142831-80-9
2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate

: 268736-70-5
(2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-ol

: 1326704-15-7
2(S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl acetate

: 1326704-13-5
(2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Guidance literature:: 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate; (2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-ol; In dichloromethane; at 20 ℃; for 0.166667h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -60 ℃; for 16h;
DOI:10.1002/chem.201100986

Reference yield:

: 1326704-09-9
(2S)-1-[(4-methoxybenzyl)oxy]-6-(trimethylsilyl)hex-5-yn-2-ol

: 1326704-15-7
2(S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl acetate

: 1326704-13-5
(2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.1: dichloromethane / 0.17 h / 20 °C / Molecular sieve

2.2: 16 h / -60 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.201100986

Reference yield:

: {4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]but-1-yn-1-yl}(trimethyl)silane

: 1326704-15-7
2(S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl acetate

: 1326704-13-5
(2S)-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: water; acetic acid / 16 h / 20 °C

2.1: di(n-butyl)tin oxide / toluene / 2 h / Reflux

2.2: 20 °C

2.3: 5 h / Reflux

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

4.1: dichloromethane / 0.17 h / 20 °C / Molecular sieve

4.2: 16 h / -60 °C

With tetrabutyl ammonium fluoride; water; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/chem.201100986