2,3,4,6-tetra-O-acetyl-O-[4-((2Z)-2-fluoro-3-hydroxyprop-1-enyl)-2-methoxyphenyl]-β-D-glucopyranoside

Base Information

Chemical Name:2,3,4,6-tetra-O-acetyl-O-[4-((2Z)-2-fluoro-3-hydroxyprop-1-enyl)-2-methoxyphenyl]-β-D-glucopyranoside
CAS No.:1333206-39-5
Molecular Formula:C₂₄H₂₉FO₁₂
Molecular Weight:528.485
Hs Code.:

Synonyms:2,3,4,6-tetra-O-acetyl-O-[4-((2Z)-2-fluoro-3-hydroxyprop-1-enyl)-2-methoxyphenyl]-β-D-glucopyranoside

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Chemical Property of 2,3,4,6-tetra-O-acetyl-O-[4-((2Z)-2-fluoro-3-hydroxyprop-1-enyl)-2-methoxyphenyl]-β-D-glucopyranoside

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Technology Process of 2,3,4,6-tetra-O-acetyl-O-[4-((2Z)-2-fluoro-3-hydroxyprop-1-enyl)-2-methoxyphenyl]-β-D-glucopyranoside

There total 3 articles about 2,3,4,6-tetra-O-acetyl-O-[4-((2Z)-2-fluoro-3-hydroxyprop-1-enyl)-2-methoxyphenyl]-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: 80.0%

: 1333206-33-9
(2Z)-2-fluoro-3-[4-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-3-methoxyphenyl]-2-propenal

: 1333206-39-5
2,3,4,6-tetra-O-acetyl-O-[4-((2Z)-2-fluoro-3-hydroxyprop-1-enyl)-2-methoxyphenyl]-β-D-glucopyranoside

Guidance literature:: (2Z)-2-fluoro-3-[4-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-3-methoxyphenyl]-2-propenal; With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -10 - 20 ℃; for 2h;

With hydrogenchloride; In tetrahydrofuran; methanol; water; pH=4;
DOI:10.1021/jo200798h

Reference yield: 78.0%

: C₂₇H₃₃FO₁₂S

: 1333206-39-5
2,3,4,6-tetra-O-acetyl-O-[4-((2Z)-2-fluoro-3-hydroxyprop-1-enyl)-2-methoxyphenyl]-β-D-glucopyranoside

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 20 ℃; for 24h;
DOI:10.1016/j.tet.2012.02.039

Reference yield:

: C₂₃H₂₆BrFO₁₁

: 1333206-39-5
2,3,4,6-tetra-O-acetyl-O-[4-((2Z)-2-fluoro-3-hydroxyprop-1-enyl)-2-methoxyphenyl]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; sodium formate; triphenylphosphine / N,N-dimethyl-formamide / 18 h / 80 °C / 30003 Torr / Autoclave; Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 2 h / -10 - 20 °C

2.2: pH 4

With bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; sodium formate; triphenylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo200798h