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

Base Information

Chemical Name:(2S)-6-iodo-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
CAS No.:1326704-16-8
Molecular Formula:C₂₈H₃₅IO₁₂
Molecular Weight:690.483
Hs Code.:

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

There total 6 articles about (2S)-6-iodo-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: 86.0%

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

: 1326704-16-8
(2S)-6-iodo-1-[(4-methoxybenzyl)oxy]hex-5-yn-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; silver nitrate; In acetone; at 20 ℃; for 2h; Darkness;
DOI:10.1002/chem.201100986

Reference yield:

: (2S)-6-(trimethylsilyl)hex-5-yne-1,2-diol

: 1326704-16-8
(2S)-6-iodo-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: di(n-butyl)tin oxide / toluene / 2 h / Reflux

1.2: 20 °C

1.3: 5 h / Reflux

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

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

3.2: 16 h / -60 °C

4.1: N-iodo-succinimide; silver nitrate / acetone / 2 h / 20 °C / Darkness

With N-iodo-succinimide; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; silver nitrate; In tetrahydrofuran; dichloromethane; acetone; toluene;
DOI:10.1002/chem.201100986

Reference yield:

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

: 1326704-16-8
(2S)-6-iodo-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 5 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

5.1: N-iodo-succinimide; silver nitrate / acetone / 2 h / 20 °C / Darkness

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